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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2501
doi:10.1107/S1600536808039950

m-Phenyl­enedi­amine

Richard Betz,a Peter Klüfersa* and Peter Mayera

aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5–13 (Haus D), 81377 München, Germany
*Correspondence e-mail: kluef@cup.uni-muenchen.de

(Received 3 November 2008; accepted 27 November 2008; online 29 November 2008)

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[Anderson, K. M., Goeta, A. E., Hancock, K. S. B. & Steed, J. W. (2006). Chem. Commun. pp. 2138-2140.]).

[Scheme 1]

Experimental

Crystal data

  • C6H8N2

  • Mr = 108.14

  • Monoclinic, P 21 /c

  • 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[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, United Kingdom.]) Tmin = 0.976, Tmax = 0.983

  • 13102 measured reflections

  • 4681 independent reflections

  • 2852 reflections with I > 2σ(I)

  • Rint = 0.031
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N11—H112⋯N33i 0.876 (17) 2.519 (17) 3.3196 (19) 152.5 (14)
N13—H131⋯N33ii 0.965 (17) 2.471 (18) 3.3312 (19) 148.2 (13)
N13—H132⋯N43iii 0.869 (14) 2.448 (15) 3.3102 (19) 171.4 (13)
N21—H211⋯N11ii 0.847 (16) 2.450 (17) 3.291 (2) 172.0 (13)
N21—H212⋯N41 0.939 (16) 2.435 (17) 3.349 (2) 164.4 (14)
N23—H231⋯N21iv 0.876 (18) 2.574 (19) 3.443 (2) 171.3 (16)
N31—H312⋯N13v 0.896 (17) 2.510 (17) 3.2668 (19) 142.4 (13)
N33—H332⋯N23 0.911 (16) 2.314 (16) 3.2025 (18) 164.9 (13)
N41—H412⋯N31vi 0.897 (18) 2.392 (17) 3.164 (2) 144.3 (15)
N11—H111⋯Cg2i 0.914 (17) 2.573 (16) 3.4260 (14) 155.8 (14)
N23—H232⋯Cg1 0.887 (18) 2.516 (17) 3.2454 (15) 139.9 (15)
N31—H311⋯Cg4vii 0.922 (17) 2.815 (16) 3.7205 (16) 166.6 (13)
N33—H331⋯Cg2iv 0.860 (16) 2.608 (15) 3.2617 (13) 133.8 (13)
N41—H411⋯Cg1viii 0.868 (18) 2.707 (17) 3.5729 (15) 174.1 (16)
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y, -z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) x-1, y+1, z; (vi) x, y-1, z; (vii) -x, -y+1, -z; (viii) x-1, y, z. C1, Cg2 and Cg4 are the centroids of the C11–C16, C21–C26 and C41–C46 phenyl rings, respectively.

Data collection: CrysAlis CCD (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, United Kingdom.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2005[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, United Kingdom.]); data reduction: CrysAlis RED; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supporting information

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

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

checkCIF report


Comment top

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).

Related literature top

For the crystal structures of a series of meta-phenylenediamine salts derived from mineralic acids, see: Anderson et al. (2006). C1, Cg2 and Cg4 are the centroids of the C11–C16, C21–C26 and C41–C46 phenyl rings, respectively.

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] 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.
[Figure 3] Fig. 3. The packing of the title compound, viewed along [-1 0 0].
m-Phenylenediamine top
Crystal data top
C6H8N2F(000) = 928
Mr = 108.14Dx = 1.231 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4885 reflections
a = 8.1350 (4) Åθ = 3.8–26.3°
b = 12.0080 (6) ŵ = 0.08 mm−1
c = 23.9003 (16) ÅT = 200 K
β = 90.818 (5)°Block, colourless
V = 2334.5 (2) Å30.32 × 0.26 × 0.22 mm
Z = 16
Data collection top
Nonius KappaCCD
diffractometer		4681 independent reflections
Radiation source: fine-focus sealed tube2852 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω scansθmax = 26.3°, θmin = 3.8°
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 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)] = 0.036Hydrogen site location: difference Fourier map
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0454P)2]
where P = (Fo2 + 2Fc2)/3
4681 reflections(Δ/σ)max < 0.001
354 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C6H8N2V = 2334.5 (2) Å3
Mr = 108.14Z = 16
Monoclinic, P21/cMo Kα radiation
a = 8.1350 (4) ŵ = 0.08 mm−1
b = 12.0080 (6) ÅT = 200 K
c = 23.9003 (16) Å0.32 × 0.26 × 0.22 mm
β = 90.818 (5)°
Data collection top
Nonius KappaCCD
diffractometer		4681 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2005)		2852 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.983Rint = 0.031
13102 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.14 e Å−3
4681 reflectionsΔρmin = −0.20 e Å−3
354 parameters
Special details top

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) top
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) top
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, º) top
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, º) top
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.

Experimental details

Crystal data
Chemical formulaC6H8N2
Mr108.14
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)8.1350 (4), 12.0080 (6), 23.9003 (16)
β (°) 90.818 (5)
V (Å3)2334.5 (2)
Z16
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.32 × 0.26 × 0.22
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2005)
Tmin, Tmax0.976, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections		13102, 4681, 2852
Rint0.031
(sin θ/λ)max (Å−1)0.623
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.088, 0.96
No. of reflections4681
No. of parameters354
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.14, −0.20

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
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.
 

Acknowledgements

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

References

First citationAnderson, K. M., Goeta, A. E., Hancock, K. S. B. & Steed, J. W. (2006). Chem. Commun. pp. 2138–2140.  Web of Science CSD CrossRef Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, Oxfordshire, United Kingdom.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 64| Part 12| December 2008| Page o2501
doi:10.1107/S1600536808039950
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