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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 70| Part 7| July 2014| Page o798
https://doi.org/10.1107/S1600536814013816

2-{4-[Bis(4-bromo­phen­yl)amino]­benzyl­­idene}malono­nitrile

Yu-Jian Zhanga and Sheng-Liang Nia*

aDepartment of Material Chemistry, Huzhou University, Huzhou, Zhejiang 313000, People's Republic of China
*Correspondence e-mail: shengliangni@163.com

(Received 23 May 2014; accepted 13 June 2014; online 21 June 2014)

In the crystal structure of the title compound, C22H13Br2N3, the two bromo­phenyl rings are rotated out of the plane of the central benzyl­idene ring by 68.7 (1) and 69.3 (1)°. Both cyano substituents are located nearly in the plane of the benzylidene ring, with the mean plane of the methylmalononitrile group being inclined to this ring by 5.8 (1)°. In the crystal, the mol­ecules are linked by weak C—H⋯N hydrogen bonds into layers parallel to the bc plane.

Keywords: crystal structure.

CCDC reference: 1008127

Similar articles

Related literature

For general background to aryl­amines such as tri­phenyl­amine as versatile optical materials, see: Ning et al. (2007[Ning, Z. J., Zhang, Q., Yan, Y. L., Qian, S. X., Cao, Y. & Tian, H. (2007). Adv. Funct. Mater. 17, 3799-3807.]); Noh et al. (2010[Noh, S. B., Kim, R. H., Kim, W. J., Kim, S., Lee, K. S., Cho, N. S., Shim, H. K., Pudavar, H. E. & Prasad, P. N. (2010). J. Mater. Chem. 20, 7422-7429.]). For related luminescent and electron-donating materials, see: Yao & Belfield (2005[Yao, S. & Belfield, K. D. (2005). J. Org. Chem. 70, 5126-5132.]); Patra et al. (2007[Patra, A., Anthony, S. P. & Radhakrishnan, T. P. (2007). Adv. Funct. Mater. 17, 2077-2084.]); Zhang et al. (2012[Zhang, Y. J., Yang, M. O., Jin, Y. X., Yu, C. H. & Zhang, C. (2012). Photochem. Photobiol. Sci. 11, 1414-1421.]). For the synthesis of the title compound, see: Chiang et al. (2005[Chiang, C. L., Shu, C. F. & Chen, C. T. (2005). Org. Lett. 7, 3717-3720.]).

[Scheme 1]

Experimental

Crystal data

  • C22H13Br2N3

  • Mr = 479.17

  • Monoclinic, P 21 /c

  • a = 14.6846 (6) Å

  • b = 10.3997 (4) Å

  • c = 13.1961 (4) Å

  • β = 103.501 (4)°

  • V = 1959.56 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 4.15 mm−1

  • T = 298 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Oxford Diffraction CrysAlis CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.369, Tmax = 0.491

  • 9075 measured reflections

  • 3843 independent reflections

  • 2702 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.094

  • S = 1.02

  • 3843 reflections

  • 244 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.57 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4A⋯N3i 0.93 2.52 3.438 (5) 169
C6—H6A⋯N2ii 0.93 2.60 3.404 (5) 145
Symmetry codes: (i) [x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1008127

Crystal structure: contains datablocks ItcLa, I. DOI: https://doi.org/10.1107/S1600536814013816/nc2326sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013816/nc2326Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013816/nc2326Isup3.cml

checkCIF report


Comment top

Arylamines such as triphenylamine (TPA) are versatile optical materials. The TPA derivatives containing the twisty arylamine exhibits good electron-donating ability and restrict the formation of an excimer complex, which further contributes to enhance fluorescence quantum efficiency (Ning et al., 2007; Noh et al., 2010). As a result, the fluorescence molecule with TPA are the excellent candidate as the luminescent and electron-donating materials (Yao & Belfield, 2005; Patra et al., 2007). Moreover, the molecular packing is relatively loose, leading to the piezofluorochromic properties due to the twisted conformation in the aggregated state. Our group always investigated the piezofluorochromic and optical properties of triphenylamine (TPA) derivatives (Zhang et al., 2012). It was found that the tiny change of the molecular structure had great effect on the piezofluorochromic behavior. The, dye DiCN-TPA with a simple molecular structure is an excellent candidate to investigate structure- property relationships. Within this project the crstal structure of the title compound was determined.

The asymmetric unit consists of one molecule in a general position (Fig. 1). In the crystal structure,the two bromophenyl groups are rotated out of the central benzylidene ring by 68.7 (1) ° and 69.3 (1) °. Both cyano substituents are located nearly in the plane of the 6-membered ring and the dihedral angle between the plane C5–C10 and N2, N3 and C1 to C4 amount to 5.8 (1) °. In the crystal, the molecules self–assemble to form a hydrogen–bonded layer parallel to the bc crystallographic plane connected by weak C—H···N hydrogen bonds(C4—H4A···N3#1 = 169 °, C4···N3#1 = 3.438 (5) Å, C6—H6A···N2#2= 145 ° and C6···N2#2 = 3.404 (5) Å) (#1 = x, 5/2 - y, 1/2 + z; #2 = 2 - x, -1/2 + y, 3/2 - z). These layers are stacked along a axis and are stabilized by van der Waals interactions.

Related literature top

For general background to arylamines such as triphenylamine as versatile optical materials, see: Ning et al. (2007); Noh et al. (2010). For related luminescent and electron-donating materials, see: Yao & Belfield (2005); Patra et al. (2007); Zhang et al. (2012). For the synthesis of the title compound, see: Chiang et al. (2005).

Experimental top

The title compound was prepared by the reaction of 4–(bis(4–bromophenyl)amino) benzaldehyde (DiBr–TPA) and malononitrile (Chiang et al.,2005) DiBr–TPA (1.3 g, 3 mmol), malononitrile (0.8 g, 12.1 mmol), and basic aluminium oxide (Al2O3, 4.0 g) are stirred in toluene (30 ml) for 18 h at 100 °C. And then, the hot solution was cooled down to room temperature, the reaction solution was filtered. The crude product was purified by column chromatography using CH2Cl2/hexane (1/50) mixture as eluent to obtain the compound (silica gel, ethyl acetate/petroleum ether: 1/9). A yellow powders was obtained with the yield of 43.1%. The yellow needle-like crystal was obtained by slowly evaporating a solution of DiCN–TPA in the mixed solvent (CH2Cl2/hexane = 1/9, v/v) at room temperature for two weeks.

Refinement top

All C—H H-atoms bonded were positioned with idealized geometry and refined isotropic with Uiso(H) = 1.2 Ueq(C) using a riding model.

Structure description top

Arylamines such as triphenylamine (TPA) are versatile optical materials. The TPA derivatives containing the twisty arylamine exhibits good electron-donating ability and restrict the formation of an excimer complex, which further contributes to enhance fluorescence quantum efficiency (Ning et al., 2007; Noh et al., 2010). As a result, the fluorescence molecule with TPA are the excellent candidate as the luminescent and electron-donating materials (Yao & Belfield, 2005; Patra et al., 2007). Moreover, the molecular packing is relatively loose, leading to the piezofluorochromic properties due to the twisted conformation in the aggregated state. Our group always investigated the piezofluorochromic and optical properties of triphenylamine (TPA) derivatives (Zhang et al., 2012). It was found that the tiny change of the molecular structure had great effect on the piezofluorochromic behavior. The, dye DiCN-TPA with a simple molecular structure is an excellent candidate to investigate structure- property relationships. Within this project the crstal structure of the title compound was determined.

The asymmetric unit consists of one molecule in a general position (Fig. 1). In the crystal structure,the two bromophenyl groups are rotated out of the central benzylidene ring by 68.7 (1) ° and 69.3 (1) °. Both cyano substituents are located nearly in the plane of the 6-membered ring and the dihedral angle between the plane C5–C10 and N2, N3 and C1 to C4 amount to 5.8 (1) °. In the crystal, the molecules self–assemble to form a hydrogen–bonded layer parallel to the bc crystallographic plane connected by weak C—H···N hydrogen bonds(C4—H4A···N3#1 = 169 °, C4···N3#1 = 3.438 (5) Å, C6—H6A···N2#2= 145 ° and C6···N2#2 = 3.404 (5) Å) (#1 = x, 5/2 - y, 1/2 + z; #2 = 2 - x, -1/2 + y, 3/2 - z). These layers are stacked along a axis and are stabilized by van der Waals interactions.

For general background to arylamines such as triphenylamine as versatile optical materials, see: Ning et al. (2007); Noh et al. (2010). For related luminescent and electron-donating materials, see: Yao & Belfield (2005); Patra et al. (2007); Zhang et al. (2012). For the synthesis of the title compound, see: Chiang et al. (2005).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound with labeling and displacement ellipsoids drawn at 45% probability level.
2-{4-[Bis(4-bromophenyl)amino]benzylidene}propanedinitrile top
Crystal data top
C22H13Br2N3F(000) = 944
Mr = 479.17Dx = 1.624 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2681 reflections
a = 14.6846 (6) Åθ = 2.9–29.3°
b = 10.3997 (4) ŵ = 4.15 mm−1
c = 13.1961 (4) ÅT = 298 K
β = 103.501 (4)°Needle-like, yellow
V = 1959.56 (12) Å30.30 × 0.20 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction CrysAlis CCD
diffractometer		3843 independent reflections
Radiation source: Enhance (Mo) X-ray Source2702 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 26.0°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		h = −18→18
Tmin = 0.369, Tmax = 0.491k = −7→12
9075 measured reflectionsl = −14→16
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0359P)2 + 1.3631P]
where P = (Fo2 + 2Fc2)/3
3843 reflections(Δ/σ)max = 0.003
244 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.57 e Å−3
Crystal data top
C22H13Br2N3V = 1959.56 (12) Å3
Mr = 479.17Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.6846 (6) ŵ = 4.15 mm−1
b = 10.3997 (4) ÅT = 298 K
c = 13.1961 (4) Å0.30 × 0.20 × 0.20 mm
β = 103.501 (4)°
Data collection top
Oxford Diffraction CrysAlis CCD
diffractometer		3843 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		2702 reflections with I > 2σ(I)
Tmin = 0.369, Tmax = 0.491Rint = 0.024
9075 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.02Δρmax = 0.38 e Å−3
3843 reflectionsΔρmin = −0.57 e Å−3
244 parameters
Special details top

Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd., 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.

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) top
xyzUiso*/Ueq
N10.7072 (2)0.7143 (3)0.4629 (2)0.0468 (7)
N21.0781 (3)1.4223 (5)0.6211 (3)0.0959 (15)
N30.9718 (2)1.2359 (4)0.3307 (3)0.0669 (10)
C11.0307 (3)1.3420 (5)0.5799 (3)0.0624 (11)
C20.9707 (2)1.2363 (4)0.4169 (3)0.0470 (9)
C30.9731 (3)1.2405 (4)0.5257 (3)0.0451 (9)
C40.9304 (3)1.1577 (4)0.5774 (3)0.0468 (9)
H4A0.94001.17490.64830.056*
C50.8725 (2)1.0472 (3)0.5432 (2)0.0414 (8)
C60.8430 (2)0.9732 (4)0.6183 (2)0.0469 (9)
H6A0.86020.99870.68770.056*
C70.7902 (3)0.8654 (4)0.5933 (2)0.0458 (9)
H7A0.77310.81810.64580.055*
C80.7612 (2)0.8249 (3)0.4900 (2)0.0407 (8)
C90.7887 (3)0.8989 (4)0.4134 (2)0.0473 (9)
H9A0.77000.87460.34380.057*
C100.8428 (2)1.0064 (4)0.4398 (2)0.0461 (9)
H10A0.86021.05360.38750.055*
C110.7119 (2)0.6094 (3)0.5341 (2)0.0413 (8)
C120.7968 (2)0.5562 (4)0.5836 (3)0.0501 (9)
H12A0.85220.59230.57420.060*
C130.8002 (2)0.4497 (4)0.6470 (3)0.0480 (9)
H13A0.85740.41370.68020.058*
C140.7180 (2)0.3981 (3)0.6603 (2)0.0426 (8)
C150.6331 (2)0.4516 (4)0.6153 (3)0.0496 (9)
H15A0.57810.41680.62690.060*
Br10.43314 (3)0.65644 (5)0.04171 (3)0.06879 (17)
C160.6305 (2)0.5586 (4)0.5520 (3)0.0484 (9)
H16A0.57330.59640.52140.058*
C170.6453 (2)0.7022 (3)0.3628 (2)0.0400 (8)
C180.6473 (3)0.5930 (4)0.3033 (3)0.0477 (9)
H18A0.69070.52850.32790.057*
C190.5850 (3)0.5793 (4)0.2072 (3)0.0502 (9)
H19A0.58610.50560.16760.060*
C200.5219 (2)0.6753 (3)0.1711 (2)0.0440 (9)
C210.5201 (3)0.7855 (4)0.2277 (3)0.0491 (9)
H21A0.47770.85070.20180.059*
C220.5820 (3)0.7985 (4)0.3238 (3)0.0482 (9)
H22A0.58100.87300.36250.058*
Br20.72147 (3)0.24595 (4)0.74116 (4)0.07151 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0552 (18)0.0382 (18)0.0415 (15)−0.0087 (16)0.0003 (13)0.0082 (13)
N20.141 (4)0.093 (3)0.055 (2)−0.065 (3)0.026 (2)−0.022 (2)
N30.073 (2)0.080 (3)0.047 (2)−0.018 (2)0.0127 (17)−0.0022 (18)
C10.087 (3)0.063 (3)0.040 (2)−0.022 (3)0.021 (2)−0.007 (2)
C20.049 (2)0.047 (2)0.044 (2)−0.0095 (19)0.0077 (16)−0.0032 (17)
C30.057 (2)0.040 (2)0.0378 (18)−0.0081 (19)0.0088 (16)−0.0075 (16)
C40.061 (2)0.045 (2)0.0330 (16)−0.003 (2)0.0094 (16)−0.0063 (16)
C50.052 (2)0.038 (2)0.0326 (16)−0.0026 (18)0.0070 (15)−0.0015 (15)
C60.063 (2)0.044 (2)0.0316 (16)−0.004 (2)0.0079 (16)−0.0021 (16)
C70.061 (2)0.045 (2)0.0321 (16)−0.004 (2)0.0119 (16)0.0054 (16)
C80.0444 (19)0.036 (2)0.0405 (17)0.0017 (17)0.0075 (15)0.0037 (15)
C90.062 (2)0.046 (2)0.0310 (17)−0.007 (2)0.0053 (16)−0.0011 (16)
C100.062 (2)0.041 (2)0.0337 (16)−0.008 (2)0.0066 (16)0.0035 (15)
C110.051 (2)0.0346 (19)0.0367 (17)−0.0033 (18)0.0079 (15)0.0022 (15)
C120.040 (2)0.053 (3)0.057 (2)−0.0042 (19)0.0122 (17)0.0134 (19)
C130.043 (2)0.046 (2)0.054 (2)0.0045 (19)0.0104 (17)0.0130 (18)
C140.052 (2)0.035 (2)0.0400 (18)−0.0036 (18)0.0094 (16)0.0011 (15)
C150.044 (2)0.049 (2)0.057 (2)−0.012 (2)0.0133 (17)0.0034 (19)
Br10.0867 (3)0.0633 (3)0.0449 (2)0.0030 (3)−0.00761 (19)−0.0020 (2)
C160.041 (2)0.051 (2)0.050 (2)0.0016 (19)0.0056 (16)0.0080 (18)
C170.046 (2)0.0343 (18)0.0387 (17)−0.0067 (18)0.0072 (15)0.0031 (15)
C180.056 (2)0.035 (2)0.049 (2)0.0065 (19)0.0071 (17)0.0022 (17)
C190.069 (2)0.038 (2)0.0426 (19)0.001 (2)0.0118 (18)−0.0046 (17)
C200.052 (2)0.041 (2)0.0370 (17)−0.0025 (19)0.0066 (15)0.0047 (16)
C210.055 (2)0.040 (2)0.049 (2)0.0092 (19)0.0045 (17)0.0026 (17)
C220.059 (2)0.036 (2)0.0460 (19)0.004 (2)0.0064 (17)−0.0016 (17)
Br20.0765 (3)0.0511 (3)0.0828 (3)−0.0111 (2)0.0102 (2)0.0252 (2)
Geometric parameters (Å, º) top
N1—C81.395 (4)C11—C121.381 (5)
N1—C171.424 (4)C12—C131.382 (5)
N1—C111.431 (4)C12—H12A0.9300
N2—C11.140 (5)C13—C141.369 (5)
N3—C21.142 (4)C13—H13A0.9300
C1—C31.436 (6)C14—C151.368 (5)
C2—C31.428 (5)C14—Br21.903 (3)
C3—C41.341 (5)C15—C161.386 (5)
C4—C51.438 (5)C15—H15A0.9300
C4—H4A0.9300Br1—C201.900 (3)
C5—C101.399 (4)C16—H16A0.9300
C5—C61.401 (5)C17—C221.382 (5)
C6—C71.359 (5)C17—C181.384 (5)
C6—H6A0.9300C18—C191.387 (5)
C7—C81.396 (4)C18—H18A0.9300
C7—H7A0.9300C19—C201.370 (5)
C8—C91.403 (5)C19—H19A0.9300
C9—C101.368 (5)C20—C211.372 (5)
C9—H9A0.9300C21—C221.384 (5)
C10—H10A0.9300C21—H21A0.9300
C11—C161.377 (5)C22—H22A0.9300
C8—N1—C17120.8 (3)C11—C12—H12A119.7
C8—N1—C11121.5 (3)C13—C12—H12A119.7
C17—N1—C11117.6 (3)C14—C13—C12118.8 (3)
N2—C1—C3178.0 (5)C14—C13—H13A120.6
N3—C2—C3177.4 (4)C12—C13—H13A120.6
C4—C3—C2126.0 (3)C15—C14—C13121.8 (3)
C4—C3—C1120.6 (3)C15—C14—Br2118.9 (3)
C2—C3—C1113.3 (3)C13—C14—Br2119.2 (3)
C3—C4—C5131.7 (3)C14—C15—C16118.8 (3)
C3—C4—H4A114.2C14—C15—H15A120.6
C5—C4—H4A114.2C16—C15—H15A120.6
C10—C5—C6116.4 (3)C11—C16—C15120.6 (3)
C10—C5—C4125.2 (3)C11—C16—H16A119.7
C6—C5—C4118.4 (3)C15—C16—H16A119.7
C7—C6—C5122.4 (3)C22—C17—C18119.0 (3)
C7—C6—H6A118.8C22—C17—N1120.7 (3)
C5—C6—H6A118.8C18—C17—N1120.3 (3)
C6—C7—C8120.8 (3)C17—C18—C19120.4 (3)
C6—C7—H7A119.6C17—C18—H18A119.8
C8—C7—H7A119.6C19—C18—H18A119.8
N1—C8—C7121.6 (3)C20—C19—C18119.5 (3)
N1—C8—C9120.6 (3)C20—C19—H19A120.3
C7—C8—C9117.7 (3)C18—C19—H19A120.3
C10—C9—C8120.8 (3)C19—C20—C21121.1 (3)
C10—C9—H9A119.6C19—C20—Br1120.3 (3)
C8—C9—H9A119.6C21—C20—Br1118.6 (3)
C9—C10—C5121.8 (3)C20—C21—C22119.2 (3)
C9—C10—H10A119.1C20—C21—H21A120.4
C5—C10—H10A119.1C22—C21—H21A120.4
C16—C11—C12119.2 (3)C17—C22—C21120.8 (3)
C16—C11—N1119.7 (3)C17—C22—H22A119.6
C12—C11—N1121.1 (3)C21—C22—H22A119.6
C11—C12—C13120.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N3i0.932.523.438 (5)169
C6—H6A···N2ii0.932.603.404 (5)145
Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N3i0.932.523.438 (5)169
C6—H6A···N2ii0.932.603.404 (5)145
Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) −x+2, y−1/2, −z+3/2.
 

Acknowledgements

The authors gratefully thank the National Natural Science Foundation of China (51203138, 51273179) and the Inter­national S&T Cooperation Program, China (2012DFA51210) for support.

References

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Volume 70| Part 7| July 2014| Page o798
https://doi.org/10.1107/S1600536814013816
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