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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2501.
Published online 2008 November 29. doi:  10.1107/S1600536808039950
PMCID: PMC2960132

m-Phenyl­enediamine

Abstract

In the title compound, C6H8N2, there are four mol­ecules in the asymmetric unit, with each mol­ecule, including the H atoms on the N atoms of the amino groups, showing local C2 symmetry. In the crystal structure, all except one of the NH2 groups participate in N—H(...)O hydrogen bonding. The identified hydrogen bonds furnish a three-dimensional network. N—H(...)π contacts are observed with H(...)π distances ranging from 2.516 (17) to 2.815 (16) Å. No π-stacking of the aromatic rings is observed.

Related literature

For the crystal structures of a series of meta-phenyl­enediamine salts derived from mineralic acids, see: Anderson et al. (2006 [triangle]).

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Object name is e-64-o2501-scheme1.jpg

Experimental

Crystal data

  • C6H8N2
  • M r = 108.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2501-efi1.jpg
  • a = 8.1350 (4) Å
  • b = 12.0080 (6) Å
  • c = 23.9003 (16) Å
  • β = 90.818 (5)°
  • V = 2334.5 (2) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 200 (2) K
  • 0.32 × 0.26 × 0.22 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2005 [triangle]) T min = 0.976, T max = 0.983
  • 13102 measured reflections
  • 4681 independent reflections
  • 2852 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.088
  • S = 0.96
  • 4681 reflections
  • 354 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808039950/ez2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039950/ez2150Isup2.hkl

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

Acknowledgments

The authors thank Professor Thomas M. Klapötke for generous allocation of diffractometer time.

supplementary crystallographic information

Comment

In a program focused on the synthesis of derivatives of phenylarsonic acid, a number of substituted aniline-derivatives were chosen as starting materials. In order to compare the influence of an arsonic group on the geometry of some of these starting materials, the crystal structure of meta-phenylenediamine was elucidated by means of single-crystal X-ray diffraction.

In the molecule (Fig. 1) bond lengths and angles are normal. The H atoms on the nitrogens in each molecule are orientated towards different sides of the aromatic plane. The asymmetric unit contains four molecules (Fig. 2).

In the crystal structure, several of the amino groups participate in a classical hydrogen bonding system. In addition, N–H···π contacts are observed with H···π distances ranging from 2.516 (17)Å to 2.815 (16)Å. Details about distances and angles of these interactions are given in Table 1 (Cgn is the centroid of the Cn1–Cn6 phenyl ring). Summarizing both these interactions, only the amino group on N43 is not involved at all. No π-stacking of the aromatic moieties is obvious. In total, a three-dimensional network is established by these interactions (Fig. 3).

Experimental

The compound was obtained commercially (Fluka). Crystals suitable for X-ray analysis were obtained upon slow evaporation of a solution of the compound in propan-2-ol.

Refinement

All H atoms bonded to C atoms were calculated in idealized position and refined as riding on their parent atoms with Uiso(H) values of 1.2 Ueq(C). All H atoms bonded to N atoms were refined freely with individual Uiso(H) values.

Figures

Fig. 1.
The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
Fig. 2.
The asymmetric unit of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
Fig. 3.
The packing of the title compound, viewed along [-1 0 0].

Crystal data

C6H8N2F000 = 928
Mr = 108.14Dx = 1.231 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4885 reflections
a = 8.1350 (4) Åθ = 3.8–26.3º
b = 12.0080 (6) ŵ = 0.08 mm1
c = 23.9003 (16) ÅT = 200 (2) K
β = 90.818 (5)ºBlock, colourless
V = 2334.5 (2) Å30.32 × 0.26 × 0.22 mm
Z = 16

Data collection

Nonius KappaCCD diffractometer4681 independent reflections
Radiation source: fine-focus sealed tube2852 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.031
T = 200(2) Kθmax = 26.3º
ω scansθmin = 3.8º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2005)h = −9→10
Tmin = 0.976, Tmax = 0.983k = −12→14
13102 measured reflectionsl = −21→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
4681 reflectionsΔρmax = 0.14 e Å3
354 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. CrysAlis RED (Oxford Diffraction, 2007) Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02); empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

xyzUiso*/Ueq
N111.03776 (15)0.37351 (12)0.21676 (6)0.0396 (3)
H1111.106 (2)0.3310 (14)0.2386 (7)0.066 (6)*
H1121.090 (2)0.4292 (14)0.2015 (7)0.058 (5)*
N130.77815 (16)0.02743 (10)0.16438 (6)0.0382 (3)
H1310.7741 (19)0.0134 (14)0.2041 (7)0.064 (5)*
H1320.6940 (17)−0.0005 (12)0.1465 (6)0.043 (4)*
N210.23465 (16)0.00605 (10)0.20759 (7)0.0402 (3)
H2110.1570 (18)−0.0254 (13)0.2248 (6)0.045 (5)*
H2120.2143 (18)0.0130 (13)0.1690 (7)0.057 (5)*
N230.52866 (15)0.35624 (11)0.19857 (7)0.0412 (3)
H2310.598 (2)0.3932 (14)0.2199 (7)0.065 (6)*
H2320.578 (2)0.3300 (14)0.1684 (8)0.061 (6)*
N31−0.00400 (16)0.84886 (11)0.09377 (7)0.0429 (3)
H311−0.089 (2)0.8489 (13)0.0677 (7)0.062 (5)*
H312−0.0368 (19)0.8796 (13)0.1259 (7)0.055 (5)*
N330.30925 (14)0.57749 (11)0.20222 (5)0.0336 (3)
H3310.3507 (18)0.6315 (13)0.2213 (7)0.052 (5)*
H3320.3850 (18)0.5226 (13)0.1973 (6)0.050 (5)*
N410.15957 (16)0.08484 (13)0.07526 (6)0.0433 (3)
H4110.088 (2)0.1238 (14)0.0935 (8)0.065 (6)*
H4120.1202 (19)0.0188 (15)0.0637 (7)0.065 (6)*
N430.51260 (16)0.09065 (13)−0.08634 (5)0.0405 (3)
H4310.547 (2)0.0217 (15)−0.0778 (7)0.066 (6)*
H4320.595 (2)0.1304 (14)−0.1029 (7)0.066 (6)*
C110.94747 (14)0.31141 (11)0.17704 (6)0.0311 (3)
C120.90693 (14)0.20145 (11)0.18897 (6)0.0293 (3)
H120.94660.16830.22260.0410 (10)*
C130.80913 (15)0.13920 (11)0.15233 (6)0.0304 (3)
C140.75103 (16)0.18860 (12)0.10305 (6)0.0352 (3)
H140.68270.14780.07780.0410 (10)*
C150.79373 (17)0.29752 (13)0.09119 (6)0.0393 (4)
H150.75520.33060.05740.0410 (10)*
C160.89083 (16)0.35915 (12)0.12736 (6)0.0372 (4)
H160.91890.43380.11840.0410 (10)*
C210.28765 (14)0.10438 (11)0.23325 (6)0.0300 (3)
C220.38064 (14)0.18093 (11)0.20319 (6)0.0289 (3)
H220.40210.16780.16480.0410 (10)*
C230.44212 (15)0.27629 (11)0.22910 (6)0.0297 (3)
C240.41196 (16)0.29445 (12)0.28552 (6)0.0357 (4)
H240.45520.35860.30380.0410 (10)*
C250.31909 (16)0.21894 (13)0.31482 (6)0.0405 (4)
H250.29780.23210.35320.0410 (10)*
C260.25634 (16)0.12459 (12)0.28946 (6)0.0362 (4)
H260.19200.07360.31030.0410 (10)*
C310.07237 (15)0.74448 (11)0.09888 (6)0.0320 (3)
C320.15676 (14)0.71468 (11)0.14764 (6)0.0299 (3)
H320.15940.76440.17860.0410 (10)*
C330.23748 (14)0.61256 (11)0.15155 (6)0.0273 (3)
C340.23643 (16)0.54176 (11)0.10574 (6)0.0332 (3)
H340.29340.47270.10750.0410 (10)*
C350.15223 (17)0.57196 (12)0.05746 (6)0.0409 (4)
H350.15120.52280.02630.0410 (10)*
C360.06989 (16)0.67165 (13)0.05351 (6)0.0394 (4)
H360.01180.69070.02010.0410 (10)*
C410.25635 (15)0.14386 (11)0.03778 (6)0.0305 (3)
C420.33350 (14)0.08948 (11)−0.00610 (5)0.0292 (3)
H420.31380.0124−0.01210.0410 (10)*
C430.43931 (15)0.14666 (12)−0.04143 (6)0.0308 (3)
C440.46499 (17)0.25939 (12)−0.03324 (6)0.0398 (4)
H440.53610.2996−0.05710.0410 (10)*
C450.38627 (17)0.31313 (12)0.00996 (7)0.0434 (4)
H450.40360.39070.01530.0410 (10)*
C460.28314 (17)0.25683 (12)0.04560 (6)0.0391 (4)
H460.23100.29520.07520.0410 (10)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N110.0309 (7)0.0345 (8)0.0532 (9)−0.0038 (6)−0.0011 (6)−0.0040 (7)
N130.0419 (7)0.0308 (8)0.0417 (9)−0.0045 (6)−0.0016 (7)−0.0037 (7)
N210.0367 (7)0.0323 (8)0.0517 (10)−0.0029 (6)0.0013 (7)−0.0033 (7)
N230.0341 (7)0.0324 (8)0.0574 (10)−0.0009 (6)0.0063 (7)−0.0003 (7)
N310.0403 (8)0.0411 (8)0.0473 (9)0.0083 (6)−0.0009 (7)0.0068 (7)
N330.0347 (7)0.0307 (7)0.0353 (8)−0.0010 (6)−0.0039 (6)−0.0004 (6)
N410.0437 (8)0.0442 (9)0.0424 (8)0.0016 (7)0.0161 (7)−0.0032 (7)
N430.0426 (7)0.0511 (9)0.0278 (7)0.0070 (7)0.0069 (6)0.0031 (7)
C110.0222 (6)0.0340 (8)0.0372 (8)0.0024 (6)0.0068 (6)−0.0039 (7)
C120.0239 (6)0.0332 (8)0.0309 (8)0.0042 (6)0.0014 (6)0.0002 (7)
C130.0272 (7)0.0319 (8)0.0322 (8)0.0028 (6)0.0086 (6)−0.0046 (7)
C140.0352 (8)0.0412 (9)0.0294 (8)−0.0012 (6)0.0023 (6)−0.0060 (7)
C150.0422 (8)0.0478 (10)0.0281 (8)0.0026 (7)0.0056 (7)0.0066 (7)
C160.0355 (8)0.0354 (9)0.0412 (9)−0.0011 (6)0.0132 (7)0.0069 (7)
C210.0230 (6)0.0298 (8)0.0370 (9)0.0044 (6)−0.0037 (6)−0.0017 (7)
C220.0256 (7)0.0323 (8)0.0287 (8)0.0061 (6)0.0008 (6)−0.0037 (6)
C230.0225 (6)0.0281 (8)0.0384 (9)0.0066 (6)−0.0010 (6)−0.0003 (7)
C240.0320 (7)0.0366 (8)0.0385 (9)0.0064 (6)−0.0062 (7)−0.0110 (7)
C250.0379 (8)0.0540 (10)0.0295 (8)0.0126 (7)0.0013 (7)−0.0067 (8)
C260.0320 (7)0.0414 (9)0.0353 (9)0.0015 (6)0.0039 (7)0.0060 (7)
C310.0259 (7)0.0325 (8)0.0375 (9)−0.0032 (6)0.0031 (6)0.0056 (7)
C320.0295 (7)0.0299 (8)0.0305 (8)−0.0033 (6)0.0027 (6)−0.0017 (6)
C330.0235 (6)0.0283 (8)0.0301 (8)−0.0053 (5)0.0016 (6)0.0024 (6)
C340.0374 (7)0.0265 (8)0.0359 (9)−0.0003 (6)0.0031 (7)−0.0008 (7)
C350.0474 (9)0.0428 (10)0.0325 (9)−0.0050 (7)0.0011 (7)−0.0076 (7)
C360.0377 (8)0.0483 (10)0.0321 (9)−0.0035 (7)−0.0043 (7)0.0037 (8)
C410.0256 (7)0.0371 (9)0.0287 (8)0.0027 (6)0.0017 (6)0.0015 (7)
C420.0291 (7)0.0297 (8)0.0288 (8)0.0013 (6)−0.0025 (6)0.0003 (6)
C430.0276 (7)0.0393 (9)0.0255 (8)0.0048 (6)−0.0027 (6)0.0012 (7)
C440.0359 (8)0.0422 (9)0.0414 (9)−0.0051 (7)0.0026 (7)0.0061 (8)
C450.0484 (9)0.0297 (9)0.0521 (10)−0.0027 (7)−0.0008 (8)−0.0025 (8)
C460.0409 (8)0.0346 (9)0.0418 (9)0.0059 (7)0.0034 (7)−0.0075 (7)

Geometric parameters (Å, °)

N11—C111.4059 (18)C15—H150.9500
N11—H1110.914 (17)C16—H160.9500
N11—H1120.876 (17)C21—C261.3924 (19)
N13—C131.3964 (18)C21—C221.3960 (18)
N13—H1310.965 (17)C22—C231.3915 (18)
N13—H1320.869 (14)C22—H220.9500
N21—C211.3959 (18)C23—C241.3913 (19)
N21—H2110.847 (16)C24—C251.378 (2)
N21—H2120.939 (16)C24—H240.9500
N23—C231.4016 (18)C25—C261.379 (2)
N23—H2310.876 (18)C25—H250.9500
N23—H2320.887 (18)C26—H260.9500
N31—C311.4034 (18)C31—C321.3910 (18)
N31—H3110.922 (17)C31—C361.3930 (19)
N31—H3120.896 (17)C32—C331.3935 (17)
N33—C331.4017 (17)C32—H320.9500
N33—H3310.860 (16)C33—C341.3862 (18)
N33—H3320.911 (16)C34—C351.3818 (19)
N41—C411.3945 (18)C34—H340.9500
N41—H4110.868 (18)C35—C361.3743 (19)
N41—H4120.897 (18)C35—H350.9500
N43—C431.4066 (18)C36—H360.9500
N43—H4310.895 (18)C41—C461.3862 (19)
N43—H4320.915 (18)C41—C421.3925 (18)
C11—C161.3912 (19)C42—C431.3950 (18)
C11—C121.3915 (18)C42—H420.9500
C12—C131.3924 (18)C43—C441.3832 (19)
C12—H120.9500C44—C451.383 (2)
C13—C141.3952 (19)C44—H440.9500
C14—C151.3837 (19)C45—C461.381 (2)
C14—H140.9500C45—H450.9500
C15—C161.3782 (19)C46—H460.9500
C11—N11—H111113.4 (10)C24—C23—C22119.55 (13)
C11—N11—H112112.2 (11)C24—C23—N23119.61 (14)
H111—N11—H112111.6 (15)C22—C23—N23120.79 (14)
C13—N13—H131112.3 (10)C25—C24—C23119.67 (13)
C13—N13—H132114.4 (10)C25—C24—H24120.2
H131—N13—H132112.3 (14)C23—C24—H24120.2
C21—N21—H211113.1 (10)C24—C25—C26121.30 (14)
C21—N21—H212113.9 (10)C24—C25—H25119.4
H211—N21—H212113.2 (14)C26—C25—H25119.4
C23—N23—H231111.7 (12)C25—C26—C21119.70 (13)
C23—N23—H232114.6 (11)C25—C26—H26120.2
H231—N23—H232110.8 (16)C21—C26—H26120.2
C31—N31—H311112.6 (10)C32—C31—C36119.49 (13)
C31—N31—H312115.5 (10)C32—C31—N31121.00 (14)
H311—N31—H312110.6 (14)C36—C31—N31119.44 (13)
C33—N33—H331112.8 (10)C31—C32—C33120.59 (13)
C33—N33—H332112.4 (10)C31—C32—H32119.7
H331—N33—H332110.7 (14)C33—C32—H32119.7
C41—N41—H411115.9 (11)C34—C33—C32119.29 (12)
C41—N41—H412117.0 (11)C34—C33—N33119.73 (12)
H411—N41—H412113.0 (15)C32—C33—N33120.82 (13)
C43—N43—H431113.6 (11)C35—C34—C33119.73 (13)
C43—N43—H432113.5 (11)C35—C34—H34120.1
H431—N43—H432110.9 (15)C33—C34—H34120.1
C16—C11—C12119.29 (13)C36—C35—C34121.42 (14)
C16—C11—N11121.41 (13)C36—C35—H35119.3
C12—C11—N11119.21 (13)C34—C35—H35119.3
C11—C12—C13121.03 (12)C35—C36—C31119.45 (13)
C11—C12—H12119.5C35—C36—H36120.3
C13—C12—H12119.5C31—C36—H36120.3
C12—C13—C14119.10 (13)C46—C41—C42119.26 (13)
C12—C13—N13119.30 (13)C46—C41—N41119.99 (14)
C14—C13—N13121.52 (13)C42—C41—N41120.67 (13)
C15—C14—C13119.46 (13)C41—C42—C43120.91 (13)
C15—C14—H14120.3C41—C42—H42119.5
C13—C14—H14120.3C43—C42—H42119.5
C16—C15—C14121.50 (13)C44—C43—C42119.30 (13)
C16—C15—H15119.3C44—C43—N43120.73 (13)
C14—C15—H15119.3C42—C43—N43119.90 (13)
C15—C16—C11119.61 (13)C45—C44—C43119.45 (14)
C15—C16—H16120.2C45—C44—H44120.3
C11—C16—H16120.2C43—C44—H44120.3
C26—C21—N21120.78 (14)C46—C45—C44121.61 (14)
C26—C21—C22119.33 (13)C46—C45—H45119.2
N21—C21—C22119.80 (13)C44—C45—H45119.2
C23—C22—C21120.44 (13)C45—C46—C41119.45 (14)
C23—C22—H22119.8C45—C46—H46120.3
C21—C22—H22119.8C41—C46—H46120.3
C16—C11—C12—C13−0.80 (18)C36—C31—C32—C33−0.47 (19)
N11—C11—C12—C13176.01 (11)N31—C31—C32—C33−177.55 (12)
C11—C12—C13—C14−0.18 (18)C31—C32—C33—C341.60 (18)
C11—C12—C13—N13176.73 (12)C31—C32—C33—N33−173.85 (11)
C12—C13—C14—C151.01 (19)C32—C33—C34—C35−1.62 (19)
N13—C13—C14—C15−175.83 (12)N33—C33—C34—C35173.87 (12)
C13—C14—C15—C16−0.9 (2)C33—C34—C35—C360.5 (2)
C14—C15—C16—C11−0.1 (2)C34—C35—C36—C310.6 (2)
C12—C11—C16—C150.94 (19)C32—C31—C36—C35−0.6 (2)
N11—C11—C16—C15−175.80 (12)N31—C31—C36—C35176.49 (12)
C26—C21—C22—C230.27 (18)C46—C41—C42—C431.22 (18)
N21—C21—C22—C23−176.38 (11)N41—C41—C42—C43−175.62 (12)
C21—C22—C23—C240.74 (18)C41—C42—C43—C44−1.28 (18)
C21—C22—C23—N23−176.83 (11)C41—C42—C43—N43−178.39 (12)
C22—C23—C24—C25−1.20 (18)C42—C43—C44—C450.42 (19)
N23—C23—C24—C25176.40 (12)N43—C43—C44—C45177.50 (12)
C23—C24—C25—C260.7 (2)C43—C44—C45—C460.5 (2)
C24—C25—C26—C210.3 (2)C44—C45—C46—C41−0.5 (2)
N21—C21—C26—C25175.81 (12)C42—C41—C46—C45−0.31 (19)
C22—C21—C26—C25−0.81 (19)N41—C41—C46—C45176.55 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N11—H112···N33i0.876 (17)2.519 (17)3.3196 (19)152.5 (14)
N13—H131···N33ii0.965 (17)2.471 (18)3.3312 (19)148.2 (13)
N13—H132···N43iii0.869 (14)2.448 (15)3.3102 (19)171.4 (13)
N21—H211···N11ii0.847 (16)2.450 (17)3.291 (2)172.0 (13)
N21—H212···N410.939 (16)2.435 (17)3.349 (2)164.4 (14)
N23—H231···N21iv0.876 (18)2.574 (19)3.443 (2)171.3 (16)
N31—H312···N13v0.896 (17)2.510 (17)3.2668 (19)142.4 (13)
N33—H332···N230.911 (16)2.314 (16)3.2025 (18)164.9 (13)
N41—H412···N31vi0.897 (18)2.392 (17)3.164 (2)144.3 (15)
N11—H111···Cg2i0.914 (17)2.573 (16)3.4260 (14)155.8 (14)
N23—H232···Cg10.887 (18)2.516 (17)3.2454 (15)139.9 (15)
N31—H311···Cg4vii0.922 (17)2.815 (16)3.7205 (16)166.6 (13)
N33—H331···Cg2iv0.860 (16)2.608 (15)3.2617 (13)133.8 (13)
N41—H411···Cg1viii0.868 (18)2.707 (17)3.5729 (15)174.1 (16)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2150).

References

  • Anderson, K. M., Goeta, A. E., Hancock, K. S. B. & Steed, J. W. (2006). Chem. Commun. pp. 2138–2140. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd., Abingdon, Oxfordshire, United Kingdom.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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