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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1162.
Published online 2010 August 25. doi:  10.1107/S1600536810033350
PMCID: PMC3007833

Poly[(μ3-4-carb­oxy­pyridine-3-carboxyl­ato-κ3 N:O 3:O 4)(triphenyl­phosphine-κP)silver(I)]

Abstract

In the title 1:1 silver(I) 4-carb­oxy­pyridine-3-carboxyl­ate adduct with triphenyl­phosphine, [Ag(C7H4NO4)(C18H15P)]n, the carboxyl­ate anion bridges the phosphine-coordinated Ag atoms through its N and O atoms, generating a coordination polymer forming layers in the bc plane. The Ag atom exists in a distorted tetra­hedral geometry. The H atom of the carboxyl­ate is midway between two O atoms of the two carboxyl groups, thus forming a strong intra­molecular hydrogen bond.

Related literature

For the synthesis of the silver reactant used in the synthesis, see: Hanna & Ng (1999 [triangle]); Ng & Othman (1997 [triangle]). For a related structure, see: Drew et al. (1971 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1162-scheme1.jpg

Experimental

Crystal data

  • [Ag(C7H4NO4)(C18H15P)]
  • M r = 536.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1162-efi4.jpg
  • a = 14.2472 (7) Å
  • b = 10.2431 (5) Å
  • c = 16.3146 (8) Å
  • β = 115.206 (1)°
  • V = 2154.18 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.04 mm−1
  • T = 100 K
  • 0.35 × 0.30 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.712, T max = 0.859
  • 13432 measured reflections
  • 4942 independent reflections
  • 4587 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.020
  • wR(F 2) = 0.055
  • S = 1.05
  • 4942 reflections
  • 293 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033350/bt5322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033350/bt5322Isup2.hkl

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

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have used bis(silver acetate.2triphenylphosphine) monohydrate sesquiethanol (Hanna & Ng, 1999; Ng & Othman, 1997) as a template in the synthesis of triphenylphosphine adducts of other silver carboxylates; the silver carboxylates themselves cannot be synthesized directly by the reaction of a silver salt with the carboxylate anion as the reaction invariably leads to the formation of some insoluble gray material.

The crystal structure of the silver(II) derivative of the monobasic 3-carboxypyridyl-4-carboxylate anion was reported a long time ago (Drew et al., 1971); the silver atom is N,O-chelated by two anions in an approximate square-planar enviroment.

The silver(I) 3-carboxypyridyl-4-carboxylate–triphenylphosphine adduct (Scheme I) exists as a polymeric compound (Fig. 1) in which the anion bridges adjacent silver atoms through one carboxyl group and the pyridyl N atom (Fig. 2). The diffraction measurements are of a sufficiently high quality for the acid H atom to be refined; the refinement places this atom mid-way between the O atoms of the two carboxyl O atoms, at a distance of 1.20 (4) Å. The O···H···O interaction is an intramolecular hydrogen bond. The pyridyl ring and the carboxyl –CO2 unit that is engaged in Ag coordination enclose a dihedral angle of 14.3 (2) ° whereas the free carboxyl group encloses a dihedral angle of 15.2 (3) ° with the pyridyl ring; such minimal twist probably locks the acid H atom in its place.

Experimental

Silver acetate (1 mmol, 0.17 g) and triphenylphosphine (2 mmol, 0.53 g) were heated in ethanol (50 ml) until the reactants dissolved completely. Gray insoluble material was removed by filtration and the solvent removed to yield bis(silver acetate.2triphenylphosphine) monohydrate sesquiethanol (Hanna & Ng, 1999; Ng & Othman, 1997).

The adduct (0.5 mmol, 0.69 g) and 3,4-pyridinedicarboxylic acid (1 mmol, 0.17 g) were placed in a convection tube; the tube was filled with a 1:1 methanol/ethanol mixture and kept at 333 K. Colorless crystals were collected after 3 days (m.p. > 550 K).

Refinement

Hydrogen atoms bonded to C were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C). The carboxylic H-atom was freely refined.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of the title polymer; ellipsoids are drawn at the 70% probability level and H atoms are of arbitrary radius. Symmetry transformations are given in Table 1.: i = 1 - x, 1 - y, 1 - z; ...

Crystal data

[Ag(C7H4NO4)(C18H15P)]F(000) = 1080
Mr = 536.25Dx = 1.653 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9293 reflections
a = 14.2472 (7) Åθ = 2.4–28.3°
b = 10.2431 (5) ŵ = 1.04 mm1
c = 16.3146 (8) ÅT = 100 K
β = 115.206 (1)°Block, colorless
V = 2154.18 (18) Å30.35 × 0.30 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer4942 independent reflections
Radiation source: fine-focus sealed tube4587 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −18→18
Tmin = 0.712, Tmax = 0.859k = −10→13
13432 measured reflectionsl = −21→20

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)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0292P)2 + 1.0816P] where P = (Fo2 + 2Fc2)/3
4942 reflections(Δ/σ)max = 0.001
293 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = −0.48 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Ag10.618798 (9)0.207715 (12)0.474714 (8)0.01345 (5)
P10.76750 (3)0.10818 (4)0.47440 (3)0.01115 (8)
O10.62846 (9)0.44669 (12)0.47885 (7)0.0165 (2)
O20.69543 (9)0.48204 (12)0.38079 (8)0.0166 (2)
O30.53857 (9)0.75596 (13)0.16600 (8)0.0193 (2)
O40.66107 (9)0.61847 (12)0.25149 (8)0.0178 (2)
H40.679 (3)0.554 (4)0.318 (2)0.095 (12)*
N10.46880 (10)0.77905 (13)0.43864 (10)0.0148 (3)
C10.78294 (12)−0.06194 (15)0.50936 (10)0.0127 (3)
C20.73968 (12)−0.10399 (16)0.56721 (11)0.0146 (3)
H20.6994−0.04530.58420.018*
C30.75513 (13)−0.23085 (17)0.60006 (11)0.0160 (3)
H30.7260−0.25870.63980.019*
C40.81319 (13)−0.31702 (16)0.57480 (11)0.0158 (3)
H4A0.8246−0.40360.59790.019*
C50.85461 (14)−0.27720 (17)0.51589 (12)0.0175 (3)
H50.8930−0.33720.49770.021*
C60.84020 (13)−0.14963 (17)0.48331 (11)0.0166 (3)
H60.8693−0.12230.44340.020*
C70.77577 (12)0.10772 (15)0.36598 (10)0.0122 (3)
C80.69787 (12)0.04132 (16)0.29445 (11)0.0159 (3)
H80.6462−0.00530.30470.019*
C90.69546 (13)0.04295 (17)0.20850 (11)0.0176 (3)
H90.6430−0.00360.16040.021*
C100.76977 (13)0.11260 (17)0.19307 (11)0.0189 (3)
H100.76700.11570.13390.023*
C110.84788 (14)0.17757 (18)0.26345 (12)0.0211 (4)
H110.89920.22410.25270.025*
C120.85148 (13)0.17507 (17)0.35027 (11)0.0173 (3)
H120.90550.21930.39860.021*
C130.88689 (12)0.18607 (16)0.55374 (11)0.0132 (3)
C140.89652 (13)0.32173 (17)0.54761 (11)0.0155 (3)
H140.84190.37040.50290.019*
C150.98636 (13)0.38491 (17)0.60728 (11)0.0185 (3)
H150.99340.47650.60240.022*
C161.06569 (13)0.31447 (18)0.67385 (12)0.0191 (3)
H161.12670.35780.71450.023*
C171.05556 (13)0.18084 (18)0.68081 (11)0.0186 (3)
H171.10960.13280.72660.022*
C180.96635 (12)0.11650 (17)0.62095 (11)0.0158 (3)
H180.95980.02490.62610.019*
C190.63603 (11)0.51340 (15)0.41887 (10)0.0127 (3)
C200.57237 (11)0.63798 (15)0.39057 (10)0.0119 (3)
C210.52976 (12)0.67522 (16)0.44994 (11)0.0130 (3)
H210.54530.62280.50220.016*
C220.44636 (13)0.85140 (18)0.36360 (12)0.0191 (3)
H220.40280.92560.35360.023*
C230.48410 (13)0.82197 (17)0.30104 (12)0.0177 (3)
H230.46570.87550.24890.021*
C240.54897 (12)0.71481 (15)0.31276 (11)0.0124 (3)
C250.58450 (12)0.69438 (16)0.23706 (11)0.0140 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.01300 (7)0.01372 (7)0.01545 (7)0.00322 (4)0.00782 (5)0.00133 (4)
P10.01137 (17)0.01234 (19)0.01010 (18)0.00181 (14)0.00492 (15)0.00062 (14)
O10.0218 (6)0.0127 (6)0.0151 (6)0.0016 (4)0.0081 (5)0.0017 (4)
O20.0175 (5)0.0186 (6)0.0147 (5)0.0052 (5)0.0077 (5)0.0007 (5)
O30.0168 (6)0.0290 (7)0.0106 (5)−0.0030 (5)0.0043 (5)0.0032 (5)
O40.0212 (6)0.0192 (6)0.0168 (6)0.0025 (5)0.0118 (5)0.0012 (5)
N10.0136 (6)0.0163 (7)0.0156 (7)0.0025 (5)0.0074 (5)0.0031 (5)
C10.0123 (7)0.0135 (7)0.0110 (7)0.0007 (6)0.0037 (6)0.0004 (6)
C20.0143 (7)0.0170 (8)0.0134 (7)0.0018 (6)0.0067 (6)−0.0013 (6)
C30.0154 (7)0.0197 (8)0.0124 (7)−0.0016 (6)0.0056 (6)0.0011 (6)
C40.0160 (7)0.0136 (8)0.0139 (7)−0.0004 (6)0.0026 (6)0.0007 (6)
C50.0184 (8)0.0162 (8)0.0188 (8)0.0035 (6)0.0088 (7)−0.0010 (6)
C60.0182 (8)0.0166 (8)0.0175 (8)0.0024 (6)0.0101 (7)0.0019 (6)
C70.0133 (7)0.0138 (8)0.0103 (7)0.0041 (6)0.0057 (6)0.0021 (6)
C80.0131 (7)0.0181 (8)0.0155 (8)0.0009 (6)0.0053 (6)0.0005 (6)
C90.0172 (7)0.0191 (8)0.0123 (7)0.0038 (6)0.0023 (6)−0.0025 (6)
C100.0262 (8)0.0205 (9)0.0119 (7)0.0066 (7)0.0097 (7)0.0016 (6)
C110.0255 (9)0.0229 (9)0.0202 (9)−0.0037 (7)0.0148 (7)−0.0001 (7)
C120.0178 (8)0.0188 (8)0.0153 (8)−0.0036 (6)0.0070 (6)−0.0026 (6)
C130.0127 (7)0.0176 (8)0.0101 (7)0.0018 (6)0.0056 (6)−0.0011 (6)
C140.0152 (7)0.0158 (8)0.0141 (7)0.0027 (6)0.0047 (6)0.0004 (6)
C150.0186 (8)0.0180 (8)0.0188 (8)−0.0004 (6)0.0078 (7)−0.0018 (7)
C160.0158 (8)0.0246 (9)0.0146 (8)−0.0008 (7)0.0041 (6)−0.0043 (7)
C170.0161 (8)0.0245 (9)0.0128 (8)0.0057 (7)0.0037 (6)0.0006 (6)
C180.0161 (7)0.0177 (8)0.0139 (7)0.0044 (6)0.0066 (6)0.0011 (6)
C190.0109 (7)0.0133 (8)0.0098 (7)−0.0009 (6)0.0007 (6)−0.0026 (6)
C200.0092 (6)0.0132 (7)0.0114 (7)−0.0010 (6)0.0027 (6)−0.0005 (6)
C210.0117 (7)0.0143 (7)0.0119 (7)−0.0008 (6)0.0041 (6)0.0016 (6)
C220.0178 (8)0.0194 (9)0.0227 (8)0.0071 (7)0.0113 (7)0.0076 (7)
C230.0161 (8)0.0213 (9)0.0165 (8)0.0038 (6)0.0078 (6)0.0083 (7)
C240.0098 (7)0.0156 (8)0.0108 (7)−0.0023 (6)0.0035 (6)−0.0005 (6)
C250.0133 (7)0.0179 (8)0.0110 (7)−0.0063 (6)0.0054 (6)−0.0031 (6)

Geometric parameters (Å, °)

Ag1—P12.3531 (4)C8—C91.388 (2)
Ag1—O12.451 (1)C8—H80.9500
Ag1—O3i2.481 (1)C9—C101.386 (2)
Ag1—N1ii2.253 (1)C9—H90.9500
P1—C11.8175 (16)C10—C111.383 (3)
P1—C71.8222 (15)C10—H100.9500
P1—C131.8248 (17)C11—C121.396 (2)
O1—C191.2353 (19)C11—H110.9500
O2—C191.2858 (18)C12—H120.9500
O3—C251.235 (2)C13—C181.391 (2)
O3—Ag1iii2.4814 (12)C13—C141.404 (2)
O4—C251.277 (2)C14—C151.394 (2)
O4—H41.20 (4)C14—H140.9500
N1—C211.335 (2)C15—C161.390 (2)
N1—C221.348 (2)C15—H150.9500
N1—Ag1ii2.2531 (13)C16—C171.386 (2)
C1—C61.396 (2)C16—H160.9500
C1—C21.397 (2)C17—C181.395 (2)
C2—C31.387 (2)C17—H170.9500
C2—H20.9500C18—H180.9500
C3—C41.387 (2)C19—C201.519 (2)
C3—H30.9500C20—C211.397 (2)
C4—C51.386 (2)C20—C241.408 (2)
C4—H4A0.9500C21—H210.9500
C5—C61.392 (2)C22—C231.374 (2)
C5—H50.9500C22—H220.9500
C6—H60.9500C23—C241.395 (2)
C7—C121.393 (2)C23—H230.9500
C7—C81.398 (2)C24—C251.536 (2)
P1—Ag1—O1113.12 (3)C9—C10—H10119.9
P1—Ag1—O3i122.95 (3)C10—C11—C12120.18 (16)
P1—Ag1—N1ii140.10 (4)C10—C11—H11119.9
O1—Ag1—O3i81.06 (4)C12—C11—H11119.9
O1—Ag1—N1ii87.84 (4)C7—C12—C11119.94 (16)
O3i—Ag1—N1ii92.57 (4)C7—C12—H12120.0
C1—P1—C7104.65 (7)C11—C12—H12120.0
C1—P1—C13104.18 (7)C18—C13—C14119.46 (15)
C7—P1—C13105.28 (7)C18—C13—P1122.35 (13)
C1—P1—Ag1113.79 (5)C14—C13—P1118.16 (12)
C7—P1—Ag1115.70 (5)C15—C14—C13119.88 (15)
C13—P1—Ag1112.16 (5)C15—C14—H14120.1
C19—O1—Ag1123.60 (10)C13—C14—H14120.1
C25—O3—Ag1iii132.51 (11)C16—C15—C14120.26 (16)
C25—O4—H4110.1 (17)C16—C15—H15119.9
C21—N1—C22116.87 (14)C14—C15—H15119.9
C21—N1—Ag1ii117.57 (10)C17—C16—C15119.88 (16)
C22—N1—Ag1ii123.80 (11)C17—C16—H16120.1
C6—C1—C2119.38 (15)C15—C16—H16120.1
C6—C1—P1121.99 (12)C16—C17—C18120.31 (16)
C2—C1—P1118.58 (12)C16—C17—H17119.8
C3—C2—C1120.45 (14)C18—C17—H17119.8
C3—C2—H2119.8C13—C18—C17120.19 (16)
C1—C2—H2119.8C13—C18—H18119.9
C2—C3—C4119.87 (15)C17—C18—H18119.9
C2—C3—H3120.1O1—C19—O2122.82 (15)
C4—C3—H3120.1O1—C19—C20117.60 (13)
C5—C4—C3120.17 (16)O2—C19—C20119.58 (14)
C5—C4—H4A119.9C21—C20—C24117.80 (14)
C3—C4—H4A119.9C21—C20—C19113.46 (13)
C4—C5—C6120.25 (15)C24—C20—C19128.70 (14)
C4—C5—H5119.9N1—C21—C20124.81 (14)
C6—C5—H5119.9N1—C21—H21117.6
C5—C6—C1119.86 (15)C20—C21—H21117.6
C5—C6—H6120.1N1—C22—C23122.51 (15)
C1—C6—H6120.1N1—C22—H22118.7
C12—C7—C8119.29 (14)C23—C22—H22118.7
C12—C7—P1123.54 (12)C22—C23—C24121.11 (15)
C8—C7—P1117.08 (11)C22—C23—H23119.4
C9—C8—C7120.46 (15)C24—C23—H23119.4
C9—C8—H8119.8C23—C24—C20116.89 (14)
C7—C8—H8119.8C23—C24—C25115.03 (14)
C10—C9—C8119.84 (15)C20—C24—C25128.06 (14)
C10—C9—H9120.1O3—C25—O4123.62 (15)
C8—C9—H9120.1O3—C25—C24117.47 (14)
C11—C10—C9120.26 (15)O4—C25—C24118.88 (14)
C11—C10—H10119.9
N1ii—Ag1—P1—C143.84 (8)C1—P1—C13—C181.57 (15)
O1—Ag1—P1—C1160.37 (6)C7—P1—C13—C18−108.28 (14)
O3i—Ag1—P1—C1−105.31 (7)Ag1—P1—C13—C18125.08 (12)
N1ii—Ag1—P1—C7165.10 (8)C1—P1—C13—C14−176.52 (12)
O1—Ag1—P1—C7−78.37 (7)C7—P1—C13—C1473.64 (14)
O3i—Ag1—P1—C715.96 (7)Ag1—P1—C13—C14−53.00 (13)
N1ii—Ag1—P1—C13−74.11 (8)C18—C13—C14—C151.6 (2)
O1—Ag1—P1—C1342.42 (6)P1—C13—C14—C15179.71 (12)
O3i—Ag1—P1—C13136.75 (7)C13—C14—C15—C16−1.1 (2)
N1ii—Ag1—O1—C19−153.23 (12)C14—C15—C16—C170.1 (3)
P1—Ag1—O1—C1961.82 (12)C15—C16—C17—C180.4 (3)
O3i—Ag1—O1—C19−60.29 (12)C14—C13—C18—C17−1.0 (2)
C7—P1—C1—C628.81 (15)P1—C13—C18—C17−179.09 (12)
C13—P1—C1—C6−81.49 (14)C16—C17—C18—C130.1 (2)
Ag1—P1—C1—C6156.05 (12)Ag1—O1—C19—O2−41.8 (2)
C7—P1—C1—C2−153.99 (12)Ag1—O1—C19—C20138.75 (11)
C13—P1—C1—C295.70 (13)O1—C19—C20—C2112.9 (2)
Ag1—P1—C1—C2−26.75 (14)O2—C19—C20—C21−166.63 (14)
C6—C1—C2—C31.3 (2)O1—C19—C20—C24−164.64 (15)
P1—C1—C2—C3−175.96 (12)O2—C19—C20—C2415.9 (2)
C1—C2—C3—C4−0.5 (2)C22—N1—C21—C200.8 (2)
C2—C3—C4—C5−0.9 (2)Ag1ii—N1—C21—C20166.32 (12)
C3—C4—C5—C61.5 (3)C24—C20—C21—N1−0.4 (2)
C4—C5—C6—C1−0.7 (3)C19—C20—C21—N1−178.22 (14)
C2—C1—C6—C5−0.7 (2)C21—N1—C22—C23−0.4 (3)
P1—C1—C6—C5176.45 (13)Ag1ii—N1—C22—C23−164.87 (13)
C1—P1—C7—C12−119.18 (14)N1—C22—C23—C24−0.5 (3)
C13—P1—C7—C12−9.67 (16)C22—C23—C24—C200.9 (2)
Ag1—P1—C7—C12114.76 (13)C22—C23—C24—C25179.83 (15)
C1—P1—C7—C864.36 (13)C21—C20—C24—C23−0.4 (2)
C13—P1—C7—C8173.86 (12)C19—C20—C24—C23176.96 (15)
Ag1—P1—C7—C8−61.70 (13)C21—C20—C24—C25−179.24 (14)
C12—C7—C8—C9−0.4 (2)C19—C20—C24—C25−1.8 (3)
P1—C7—C8—C9176.25 (12)Ag1iii—O3—C25—O493.68 (18)
C7—C8—C9—C10−1.0 (2)Ag1iii—O3—C25—C24−88.43 (17)
C8—C9—C10—C111.7 (3)C23—C24—C25—O3−13.6 (2)
C9—C10—C11—C12−1.0 (3)C20—C24—C25—O3165.22 (15)
C8—C7—C12—C111.1 (2)C23—C24—C25—O4164.40 (15)
P1—C7—C12—C11−175.27 (13)C20—C24—C25—O4−16.8 (2)
C10—C11—C12—C7−0.5 (3)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4···O21.20 (4)1.20 (4)2.401 (2)176 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5322).

References

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