PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1430.
Published online 2010 October 23. doi:  10.1107/S1600536810041577
PMCID: PMC3009345

Tetra­kis(1H-imidazole-κN 3)(2-phenyl­propanedioato-κ2 O 1,O 3)nickel(II)

Abstract

In the title complex, [Ni(C9H6O4)(C3H4N2)4], the NiII ion is O,O′-chelated by the phenyl­malonato ligand and coordinated by four imidazole ligands in a slightly distorted octa­hedral geometry. In the crystal structure, symmetry-related mol­ecules are linked by N—H(...)O hydrogen bonds, generating a three-dimensional network.

Related literature

For the cobalt(II) analog, see: Zhang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1430-scheme1.jpg

Experimental

Crystal data

  • [Ni(C9H6O4)(C3H4N2)4]
  • M r = 509.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1430-efi1.jpg
  • a = 8.5358 (8) Å
  • b = 13.3148 (12) Å
  • c = 20.6996 (19) Å
  • V = 2352.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.87 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.812, T max = 0.881
  • 15962 measured reflections
  • 5516 independent reflections
  • 4013 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.086
  • S = 0.98
  • 5516 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.31 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2344 Friedel pairs
  • Flack parameter: 0.082 (13)

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041577/lh5153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041577/lh5153Isup2.hkl

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

Acknowledgments

We thank the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province, Yangzhou University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have previously reported the crystal structure of the tetrakis(imidazole) adduct of cobalt(II) phenylmalonate. The structure features the carboxylate-chelated cobalt(II) atom bonded to four N-heterocycles; each of these has a nitrogen-donor site that enables the octahedrally coordinated mononuclear molecule to connect with each other to form a three-dimensional network (Zhang et al., 2007). The nickel analog (Fig. 1) is isostructural, the two compounds crystallizing with similar unit cell dimensions.

Experimental

Imidazole (0.339 g. 0.56 mmol) was dissolved in methanol (10 ml) and to the solution was added nickel nitrate hexahydrate (0.480 g, 1.65 mmol) dissolved in water (6 ml). To the clear soluiton was added phenylmalonic acid (0.300 g, 1.65 mmol) and sodium hydroxide (0.120 g, 3.30 mmol) dissolved in water (10 ml). The filtered solution was set aside for the growth of green crystals over several days; yield 50%. CH&N elemental analysis. Calc. for C21H22N8NiO4: C 49.53, H 4.36, N 22.00%. Found: C 49.61, H 4.49, N 21.91%.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

The imidazolium H-atoms were similarly treated (N–H 0.88 Å; Uiso(H) 1.2Ueq(N)).

The crystal has several voids but these are too small (20Å3) to accomodate a solvent molecule.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of Ni(C3H4N2)4(C9H6O4) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

[Ni(C9H6O4)(C3H4N2)4]F(000) = 1056
Mr = 509.18Dx = 1.438 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2481 reflections
a = 8.5358 (8) Åθ = 2.6–21.7°
b = 13.3148 (12) ŵ = 0.87 mm1
c = 20.6996 (19) ÅT = 293 K
V = 2352.6 (4) Å3Prism, green
Z = 40.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer5516 independent reflections
Radiation source: fine-focus sealed tube4013 reflections with I > 2σ(I)
graphiteRint = 0.051
ω scansθmax = 27.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.812, Tmax = 0.881k = −17→17
15962 measured reflectionsl = −19→27

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.086w = 1/[σ2(Fo2) + (0.0326P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
5516 reflectionsΔρmax = 0.41 e Å3
307 parametersΔρmin = −0.31 e Å3
0 restraintsAbsolute structure: Flack (1983), 2344 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.082 (13)

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

xyzUiso*/Ueq
Ni10.66167 (4)0.40568 (3)0.336577 (18)0.02636 (10)
O10.8851 (2)0.40575 (17)0.29819 (9)0.0324 (4)
O21.0679 (2)0.37546 (16)0.22649 (12)0.0433 (6)
O30.5823 (2)0.41866 (15)0.24132 (9)0.0323 (5)
O40.6203 (3)0.43579 (17)0.13674 (11)0.0515 (7)
N10.6652 (3)0.24683 (16)0.33088 (13)0.0338 (6)
N20.5969 (3)0.0939 (2)0.30389 (16)0.0597 (9)
H20.53880.04320.29080.072*
N30.4310 (2)0.4058 (2)0.37002 (11)0.0301 (5)
N40.1739 (3)0.4091 (2)0.36620 (12)0.0388 (6)
H40.07820.41100.35040.047*
N50.6703 (3)0.56328 (16)0.33579 (12)0.0312 (5)
N60.7570 (3)0.7169 (2)0.32201 (14)0.0424 (8)
H60.81800.76670.30980.051*
N70.7489 (3)0.4034 (2)0.43160 (11)0.0324 (6)
N80.8143 (4)0.4576 (2)0.52810 (14)0.0500 (8)
H80.83590.49910.55990.060*
C10.9291 (3)0.3761 (2)0.24304 (17)0.0300 (7)
C20.8045 (3)0.3333 (2)0.19607 (15)0.0343 (8)
H2A0.76620.27130.21610.041*
C30.6602 (3)0.4033 (2)0.19068 (14)0.0315 (6)
C40.8732 (3)0.3022 (2)0.13164 (16)0.0361 (8)
C50.8607 (4)0.2032 (3)0.11128 (17)0.0468 (9)
H50.80550.15690.13600.056*
C60.9301 (5)0.1738 (3)0.0545 (2)0.0635 (12)
H6A0.92020.10750.04100.076*
C71.0126 (5)0.2392 (4)0.0179 (2)0.0683 (13)
H71.06020.2173−0.01990.082*
C81.0264 (5)0.3368 (3)0.0363 (2)0.0643 (12)
H8A1.08310.38170.01100.077*
C90.9556 (4)0.3689 (3)0.09264 (17)0.0471 (9)
H90.96320.43600.10470.057*
C100.5503 (4)0.1886 (2)0.31110 (17)0.0450 (9)
H100.44880.21080.30310.054*
C110.7919 (4)0.1839 (2)0.3360 (2)0.0493 (9)
H110.89200.20360.34840.059*
C120.7502 (4)0.0899 (3)0.3204 (2)0.0626 (12)
H120.81390.03330.32080.075*
C130.3064 (3)0.4087 (2)0.33245 (16)0.0361 (7)
H130.31060.41020.28760.043*
C140.3722 (3)0.4050 (3)0.43166 (15)0.0391 (7)
H140.43180.40400.46930.047*
C150.2137 (4)0.4060 (3)0.42918 (17)0.0446 (8)
H150.14540.40480.46420.054*
C160.7835 (4)0.6195 (2)0.31334 (16)0.0383 (8)
H160.87280.59410.29350.046*
C170.5650 (4)0.6304 (2)0.36077 (17)0.0427 (9)
H170.47050.61320.38020.051*
C180.6178 (4)0.7249 (2)0.35329 (17)0.0426 (9)
H180.56900.78370.36680.051*
C190.7768 (4)0.4830 (3)0.46802 (16)0.0392 (8)
H190.77090.54890.45330.047*
C200.7710 (5)0.3241 (3)0.47194 (18)0.0585 (12)
H200.75900.25710.46040.070*
C210.8133 (6)0.3571 (3)0.53140 (18)0.0682 (13)
H210.83680.31790.56730.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.02413 (16)0.02630 (16)0.02864 (19)−0.00065 (17)−0.00168 (18)−0.00153 (19)
O10.0262 (10)0.0397 (11)0.0312 (11)−0.0002 (10)0.0005 (9)−0.0080 (11)
O20.0255 (11)0.0565 (15)0.0479 (15)0.0019 (10)0.0034 (11)−0.0166 (12)
O30.0296 (10)0.0422 (13)0.0252 (11)0.0041 (10)0.0009 (9)−0.0002 (10)
O40.0486 (14)0.0700 (17)0.0359 (14)0.0183 (12)0.0071 (12)0.0217 (12)
N10.0380 (13)0.0312 (13)0.0322 (15)−0.0052 (12)−0.0028 (18)0.0004 (11)
N20.0581 (18)0.0281 (14)0.093 (3)−0.0143 (16)−0.0013 (17)−0.0146 (18)
N30.0258 (11)0.0332 (12)0.0313 (14)−0.0023 (13)−0.0017 (11)−0.0005 (14)
N40.0232 (11)0.0497 (15)0.0436 (15)0.0030 (15)−0.0003 (13)0.0011 (15)
N50.0278 (12)0.0303 (12)0.0356 (14)−0.0031 (10)0.0006 (17)−0.0003 (11)
N60.0387 (15)0.0343 (15)0.054 (2)−0.0088 (13)−0.0008 (14)0.0059 (15)
N70.0331 (12)0.0349 (13)0.0291 (14)0.0015 (13)−0.0029 (11)−0.0033 (15)
N80.064 (2)0.053 (2)0.0330 (18)0.0026 (18)−0.0074 (17)−0.0125 (15)
C10.0243 (15)0.0255 (16)0.040 (2)0.0061 (12)−0.0016 (14)−0.0010 (13)
C20.0326 (18)0.0358 (17)0.0346 (18)−0.0004 (14)0.0001 (15)0.0012 (15)
C30.0283 (13)0.0343 (14)0.0319 (15)−0.0006 (18)0.0009 (14)−0.0023 (15)
C40.0273 (16)0.049 (2)0.0322 (17)0.0077 (15)−0.0009 (14)−0.0051 (16)
C50.0362 (18)0.051 (2)0.053 (2)0.0041 (18)−0.0058 (18)−0.0053 (18)
C60.064 (3)0.069 (3)0.057 (3)0.018 (2)−0.007 (2)−0.031 (2)
C70.075 (3)0.088 (3)0.042 (3)0.032 (3)−0.001 (2)−0.013 (2)
C80.060 (3)0.088 (3)0.045 (3)0.018 (2)0.015 (2)0.015 (2)
C90.052 (2)0.048 (2)0.042 (2)0.0090 (17)0.0023 (19)0.0043 (17)
C100.0379 (18)0.0350 (18)0.062 (3)−0.0055 (15)0.0071 (17)−0.0004 (17)
C110.0431 (19)0.0379 (18)0.067 (3)0.0085 (14)−0.018 (2)−0.004 (2)
C120.056 (2)0.0342 (19)0.098 (4)0.006 (2)−0.009 (2)−0.003 (3)
C130.0293 (14)0.0416 (16)0.0374 (17)−0.0031 (14)−0.0022 (14)−0.0015 (19)
C140.0350 (16)0.0509 (18)0.0313 (17)0.0019 (18)−0.0008 (14)0.0026 (18)
C150.0366 (16)0.056 (2)0.041 (2)0.0009 (19)0.0089 (15)0.006 (2)
C160.0365 (17)0.0314 (19)0.047 (2)0.0011 (13)0.0027 (15)−0.0013 (15)
C170.0347 (17)0.0400 (18)0.053 (2)0.0016 (14)0.0081 (17)0.0003 (16)
C180.0430 (19)0.0261 (16)0.059 (3)0.0068 (14)0.0016 (17)0.0031 (15)
C190.0401 (19)0.044 (2)0.034 (2)−0.0004 (16)−0.0038 (16)−0.0028 (17)
C200.102 (3)0.038 (2)0.036 (2)0.003 (2)−0.020 (2)0.0050 (17)
C210.112 (4)0.057 (3)0.036 (2)0.006 (3)−0.025 (3)0.0050 (19)

Geometric parameters (Å, °)

Ni1—O12.0662 (18)C2—C41.515 (4)
Ni1—N32.087 (2)C2—C31.549 (4)
Ni1—O32.092 (2)C2—H2A0.9800
Ni1—N52.100 (2)C4—C51.388 (5)
Ni1—N72.103 (2)C4—C91.391 (4)
Ni1—N12.118 (2)C5—C61.372 (5)
O1—C11.265 (4)C5—H50.9300
O2—C11.234 (3)C6—C71.352 (6)
O3—C31.258 (3)C6—H6A0.9300
O4—C31.245 (3)C7—C81.359 (5)
N1—C101.316 (4)C7—H70.9300
N1—C111.373 (4)C8—C91.382 (5)
N2—C101.330 (4)C8—H8A0.9300
N2—C121.353 (4)C9—H90.9300
N2—H20.8800C10—H100.9300
N3—C131.318 (3)C11—C121.340 (5)
N3—C141.371 (4)C11—H110.9300
N4—C131.329 (3)C12—H120.9300
N4—C151.348 (4)C13—H130.9300
N4—H40.8800C14—C151.355 (4)
N5—C161.308 (4)C14—H140.9300
N5—C171.369 (4)C15—H150.9300
N6—C161.329 (4)C16—H160.9300
N6—C181.357 (4)C17—C181.345 (4)
N6—H60.8800C17—H170.9300
N7—C191.323 (4)C18—H180.9300
N7—C201.359 (4)C19—H190.9300
N8—C191.328 (4)C20—C211.356 (5)
N8—C211.339 (4)C20—H200.9300
N8—H80.8800C21—H210.9300
C1—C21.550 (4)
O1—Ni1—N3176.75 (9)C5—C4—C2119.8 (3)
O1—Ni1—O386.37 (7)C9—C4—C2122.2 (3)
N3—Ni1—O390.39 (8)C6—C5—C4119.9 (4)
O1—Ni1—N587.95 (9)C6—C5—H5120.1
N3—Ni1—N591.98 (10)C4—C5—H5120.1
O3—Ni1—N585.50 (9)C7—C6—C5121.4 (4)
O1—Ni1—N791.88 (8)C7—C6—H6A119.3
N3—Ni1—N791.36 (9)C5—C6—H6A119.3
O3—Ni1—N7175.72 (9)C6—C7—C8120.3 (4)
N5—Ni1—N790.54 (10)C6—C7—H7119.9
O1—Ni1—N188.05 (10)C8—C7—H7119.9
N3—Ni1—N191.88 (10)C7—C8—C9119.6 (4)
O3—Ni1—N191.98 (9)C7—C8—H8A120.2
N5—Ni1—N1175.40 (10)C9—C8—H8A120.2
N7—Ni1—N191.87 (10)C8—C9—C4120.9 (4)
C1—O1—Ni1128.36 (18)C8—C9—H9119.5
C3—O3—Ni1126.92 (18)C4—C9—H9119.5
C10—N1—C11104.6 (2)N1—C10—N2111.8 (3)
C10—N1—Ni1126.6 (2)N1—C10—H10124.1
C11—N1—Ni1128.0 (2)N2—C10—H10124.1
C10—N2—C12107.3 (3)C12—C11—N1110.0 (3)
C10—N2—H2126.3C12—C11—H11125.0
C12—N2—H2126.3N1—C11—H11125.0
C13—N3—C14104.7 (2)C11—C12—N2106.3 (4)
C13—N3—Ni1124.44 (19)C11—C12—H12126.8
C14—N3—Ni1130.84 (18)N2—C12—H12126.8
C13—N4—C15107.1 (2)N3—C13—N4112.1 (3)
C13—N4—H4126.5N3—C13—H13123.9
C15—N4—H4126.5N4—C13—H13123.9
C16—N5—C17104.2 (3)C15—C14—N3109.3 (3)
C16—N5—Ni1126.9 (2)C15—C14—H14125.4
C17—N5—Ni1128.8 (2)N3—C14—H14125.4
C16—N6—C18106.8 (3)N4—C15—C14106.8 (3)
C16—N6—H6126.6N4—C15—H15126.6
C18—N6—H6126.6C14—C15—H15126.6
C19—N7—C20104.3 (3)N5—C16—N6112.7 (3)
C19—N7—Ni1125.8 (2)N5—C16—H16123.7
C20—N7—Ni1129.4 (2)N6—C16—H16123.7
C19—N8—C21107.5 (3)C18—C17—N5110.3 (3)
C19—N8—H8126.2C18—C17—H17124.8
C21—N8—H8126.2N5—C17—H17124.8
O2—C1—O1122.5 (3)C17—C18—N6106.0 (3)
O2—C1—C2118.9 (3)C17—C18—H18127.0
O1—C1—C2118.5 (3)N6—C18—H18127.0
C4—C2—C3114.1 (2)N7—C19—N8111.9 (3)
C4—C2—C1112.8 (2)N7—C19—H19124.1
C3—C2—C1111.7 (2)N8—C19—H19124.1
C4—C2—H2A105.8C21—C20—N7110.1 (3)
C3—C2—H2A105.8C21—C20—H20125.0
C1—C2—H2A105.8N7—C20—H20125.0
O4—C3—O3123.1 (3)N8—C21—C20106.2 (4)
O4—C3—C2119.4 (3)N8—C21—H21126.9
O3—C3—C2117.2 (3)C20—C21—H21126.9
C5—C4—C9118.0 (3)
O3—Ni1—O1—C1−28.3 (3)Ni1—O3—C3—O4−161.4 (2)
N5—Ni1—O1—C1−113.9 (3)Ni1—O3—C3—C223.8 (4)
N7—Ni1—O1—C1155.7 (3)C4—C2—C3—O4−6.3 (4)
N1—Ni1—O1—C163.9 (3)C1—C2—C3—O4123.0 (3)
O1—Ni1—O3—C315.1 (2)C4—C2—C3—O3168.7 (3)
N3—Ni1—O3—C3−164.7 (2)C1—C2—C3—O3−61.9 (4)
N5—Ni1—O3—C3103.4 (2)C3—C2—C4—C5−111.2 (3)
N1—Ni1—O3—C3−72.8 (2)C1—C2—C4—C5120.0 (3)
O1—Ni1—N1—C10−137.2 (3)C3—C2—C4—C971.8 (4)
N3—Ni1—N1—C1039.6 (3)C1—C2—C4—C9−57.1 (4)
O3—Ni1—N1—C10−50.9 (3)C9—C4—C5—C60.6 (5)
N7—Ni1—N1—C10131.0 (3)C2—C4—C5—C6−176.6 (3)
O1—Ni1—N1—C1130.7 (3)C4—C5—C6—C70.8 (6)
N3—Ni1—N1—C11−152.6 (3)C5—C6—C7—C8−1.1 (7)
O3—Ni1—N1—C11117.0 (3)C6—C7—C8—C90.1 (7)
N7—Ni1—N1—C11−61.1 (3)C7—C8—C9—C41.4 (6)
O3—Ni1—N3—C132.8 (3)C5—C4—C9—C8−1.7 (5)
N5—Ni1—N3—C1388.3 (3)C2—C4—C9—C8175.4 (3)
N7—Ni1—N3—C13178.9 (3)C11—N1—C10—N20.3 (4)
N1—Ni1—N3—C13−89.2 (3)Ni1—N1—C10—N2170.4 (2)
O3—Ni1—N3—C14−175.9 (3)C12—N2—C10—N10.5 (4)
N5—Ni1—N3—C14−90.4 (3)C10—N1—C11—C12−1.0 (4)
N7—Ni1—N3—C140.2 (3)Ni1—N1—C11—C12−171.0 (3)
N1—Ni1—N3—C1492.1 (3)N1—C11—C12—N21.3 (5)
O1—Ni1—N5—C163.4 (3)C10—N2—C12—C11−1.1 (5)
N3—Ni1—N5—C16−173.4 (3)C14—N3—C13—N4−0.4 (4)
O3—Ni1—N5—C16−83.1 (3)Ni1—N3—C13—N4−179.4 (2)
N7—Ni1—N5—C1695.3 (3)C15—N4—C13—N3−0.2 (4)
O1—Ni1—N5—C17−173.2 (3)C13—N3—C14—C150.8 (4)
N3—Ni1—N5—C1710.1 (3)Ni1—N3—C14—C15179.7 (2)
O3—Ni1—N5—C17100.3 (3)C13—N4—C15—C140.7 (4)
N7—Ni1—N5—C17−81.3 (3)N3—C14—C15—N4−1.0 (4)
O1—Ni1—N7—C1992.3 (2)C17—N5—C16—N6−0.3 (4)
N3—Ni1—N7—C19−87.6 (3)Ni1—N5—C16—N6−177.6 (2)
N5—Ni1—N7—C194.4 (3)C18—N6—C16—N51.1 (4)
N1—Ni1—N7—C19−179.5 (3)C16—N5—C17—C18−0.5 (4)
O1—Ni1—N7—C20−96.5 (3)Ni1—N5—C17—C18176.7 (2)
N3—Ni1—N7—C2083.5 (3)N5—C17—C18—N61.2 (4)
N5—Ni1—N7—C20175.5 (3)C16—N6—C18—C17−1.3 (4)
N1—Ni1—N7—C20−8.4 (3)C20—N7—C19—N8−0.1 (4)
Ni1—O1—C1—O2−176.5 (2)Ni1—N7—C19—N8172.8 (2)
Ni1—O1—C1—C2−0.1 (4)C21—N8—C19—N70.9 (5)
O2—C1—C2—C4−4.3 (4)C19—N7—C20—C21−0.6 (5)
O1—C1—C2—C4179.1 (3)Ni1—N7—C20—C21−173.2 (3)
O2—C1—C2—C3−134.4 (3)C19—N8—C21—C20−1.2 (6)
O1—C1—C2—C349.0 (4)N7—C20—C21—N81.2 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.882.062.943 (3)176
N4—H4···O1ii0.881.972.839 (3)168
N6—H6···O2iii0.881.902.774 (3)172
N8—H8···O4iv0.881.852.718 (3)169

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+2, y+1/2, −z+1/2; (iv) −x+3/2, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5153).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.
  • Zhang, K.-L., Kuai, H.-W., Liu, W.-L. & Diao, G.-W. (2007). J. Mol. Struct.831, 114–118.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography