supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2008). E64, o1980    [ doi:10.1107/S1600536808029784 ]

2,2',2''-[Nitrilotris(methylene-p-phenylene)]tribenzonitrile

L.-Z. Chen

Abstract top

In the title compound, C42H30N4, the conformations of the three wings of the molecule are not similar to each other as the torsion angles between the planes of the benzene rings are significantly different. In addition to van der Waals interactions, the crystal structure is stabilized only by intramolecular C-H...N hydrogen bonds.

Comment top

Tripodal ligands have shown tremendous scope in the synthesis of transition-metal complexes. Perhaps the most extensively studied examples are those comprising tris-(2-pyridylmethyl)amine, which has been widely exploited in complexes (Fox et al. 1996; Menage et al. 1992; Murthy & Karlin 1993), tris(2-aminobenzyl)amine (Foces-Foces et al. 1999), tris(2-chlorobenzl)amine and tris(2-bromobenzyl)amine (Chen et al. 2005) and tribenzylamine (Iwasaki & Iwasaki 1972). The construction of new members of this family of ligands is an important direction in the development of modern coordination chemistry (Schrock 1997). We report here the crystal structure of the title compound tris[4-(2-cyano-phenyl)benzyl]amine, (I).

In the title compound (Fig.1), the conformations of the three wings of the molecule do not appear to be similar as the torsion angles between the planes of benzene rings are significantly different from each other. The pairs of benzene rings in the three wings form dihedral angle of 47.70 (10)°, 54.36 (7)° and 87.89 (9)°, respectively. In addition to van der Waals interactions, the crystal structure is stabilized only by intramolecular C—H···N hydrogen bonds: C4—H4A···N3 and C24—H24A···N2 (Table 1).

Related literature top

For related structures, see: Fox et al. (1996); Menage et al. (1992); Murthy & Karlin (1993); Schrock (1997); Foces-Foces et al. (1999); Chen et al. (2005); Iwasaki & Iwasaki (1972).

Experimental top

The title compount was obtained from the combination of 2-cyano-4'-(bromomethyl)biphenyl (8.13 g, 30.0 mmol) with 29% aqueous ammonia (2.64 g, 45.0 mmol) in ethanol (50 ml) at room temperature. A white solid precipitated during stirring over 24 h. The precipitate was collected by filtration, washed with ethanol, and allowed to air-dry to yield 2.67 g (43%) of colorless microcrystals. Recrystallization was effected from hot acetonitrile to yield colorless blocks suitable for X-ray analysis.

Refinement top

All H atoms were fixed geometrically and treated as riding with C–H = 0.93 Å(aromatic), 0.97 Å(methylene), and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
2,2',2''-[Nitrilotris(methylene-p-phenylene)]tribenzonitrile top
Crystal data top
C42H30N4F(000) = 1240
Mr = 590.70Dx = 1.193 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7512 reflections
a = 21.257 (4) Åθ = 3.2–27.5°
b = 15.085 (3) ŵ = 0.07 mm−1
c = 10.294 (2) ÅT = 298 K
β = 94.73 (3)°Block, colorless
V = 3289.5 (11) Å30.27 × 0.18 × 0.15 mm
Z = 4
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer		7524 independent reflections
Radiation source: fine-focus sealed tube4007 reflections with I > 2σ(I)
graphiteRint = 0.081
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = −27→27
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −19→19
Tmin = 0.985, Tmax = 0.989l = −13→13
32746 measured reflections
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0804P)2 + 0.198P]
where P = (Fo2 + 2Fc2)/3
7524 reflections(Δ/σ)max < 0.001
415 parametersΔρmax = 0.17 e Å−3
6 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C42H30N4V = 3289.5 (11) Å3
Mr = 590.70Z = 4
Monoclinic, P21/cMo Kα radiation
a = 21.257 (4) ŵ = 0.07 mm−1
b = 15.085 (3) ÅT = 298 K
c = 10.294 (2) Å0.27 × 0.18 × 0.15 mm
β = 94.73 (3)°
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer		7524 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		4007 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.989Rint = 0.081
32746 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.187Δρmax = 0.17 e Å−3
S = 1.02Δρmin = −0.24 e Å−3
7524 reflectionsAbsolute structure: ?
415 parametersFlack parameter: ?
6 restraintsRogers parameter: ?
Special details top

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
C10.10835 (14)0.41593 (18)0.1399 (3)0.0704 (7)
C20.04158 (12)0.40234 (15)0.1365 (3)0.0635 (7)
C30.00882 (16)0.39289 (18)0.0152 (3)0.0819 (9)
H3A0.03020.3986−0.05960.098*
C4−0.05428 (19)0.3753 (2)0.0036 (4)0.0946 (11)
H4A−0.07590.3692−0.07810.114*
C5−0.08530 (15)0.3669 (2)0.1143 (4)0.0947 (11)
H5A−0.12830.35460.10680.114*
C6−0.05411 (12)0.37614 (18)0.2376 (3)0.0818 (9)
H6A−0.07630.36950.31130.098*
C70.01046 (11)0.39535 (14)0.2513 (3)0.0604 (7)
C80.04395 (10)0.40436 (15)0.3830 (3)0.0576 (6)
C90.08923 (11)0.46989 (15)0.4118 (3)0.0613 (7)
H9A0.09680.51200.34890.074*
C100.12276 (11)0.47328 (16)0.5310 (3)0.0623 (7)
H10A0.15290.51750.54700.075*
C110.11309 (11)0.41278 (15)0.6284 (2)0.0559 (6)
C120.06633 (12)0.35033 (17)0.6025 (3)0.0706 (7)
H12A0.05720.31050.66730.085*
C130.03285 (12)0.34602 (17)0.4821 (3)0.0720 (8)
H13A0.00200.30270.46710.086*
C140.15284 (11)0.41551 (17)0.7558 (2)0.0621 (7)
H14A0.15250.47520.79090.074*
H14B0.13480.37620.81740.074*
C150.25982 (12)0.41470 (14)0.8554 (2)0.0545 (6)
H15A0.30000.38450.85330.065*
H15B0.24090.39580.93340.065*
C160.27119 (10)0.51310 (14)0.8625 (2)0.0499 (6)
C170.29125 (16)0.55906 (17)0.7584 (2)0.0854 (9)
H17A0.29690.52880.68150.103*
C180.30323 (16)0.64887 (17)0.7647 (2)0.0843 (9)
H18A0.31660.67810.69230.101*
C190.29559 (10)0.69558 (14)0.8768 (2)0.0471 (5)
C200.27620 (13)0.64986 (16)0.9803 (2)0.0674 (7)
H20A0.27100.68001.05750.081*
C210.26400 (12)0.56002 (16)0.9737 (2)0.0641 (7)
H21A0.25070.53101.04630.077*
C220.31100 (10)0.79189 (13)0.8858 (2)0.0458 (5)
C230.37045 (12)0.82099 (15)0.9309 (2)0.0615 (7)
H23A0.40120.77940.95710.074*
C240.38549 (13)0.90998 (16)0.9382 (2)0.0641 (7)
H24A0.42600.92750.96820.077*
C250.34097 (13)0.97222 (16)0.9014 (2)0.0601 (6)
H25A0.35111.03220.90650.072*
C260.28152 (13)0.94626 (15)0.8570 (3)0.0657 (7)
H26A0.25120.98860.83180.079*
C270.26623 (11)0.85714 (15)0.8493 (2)0.0556 (6)
C280.20387 (15)0.83188 (18)0.8029 (3)0.0873 (10)
C290.22125 (11)0.29298 (14)0.7186 (2)0.0548 (6)
H29A0.18670.27610.65610.066*
H29B0.21540.26270.79980.066*
C300.28224 (10)0.26225 (13)0.6692 (2)0.0456 (5)
C310.31594 (11)0.31379 (14)0.5885 (2)0.0570 (6)
H31A0.30170.37070.56720.068*
C320.37013 (11)0.28319 (15)0.5387 (2)0.0572 (6)
H32A0.39200.31970.48520.069*
C330.39231 (10)0.19792 (14)0.5679 (2)0.0455 (5)
C340.35817 (10)0.14595 (13)0.6485 (2)0.0472 (5)
H34A0.37170.08860.66890.057*
C350.30462 (10)0.17814 (13)0.6985 (2)0.0473 (5)
H35A0.28300.14230.75340.057*
C360.44926 (10)0.16442 (13)0.5103 (2)0.0480 (5)
C370.45515 (12)0.17505 (16)0.3787 (3)0.0653 (7)
H37A0.42300.20330.32760.078*
C380.50730 (14)0.14503 (19)0.3209 (3)0.0791 (8)
H38A0.50990.15310.23190.095*
C390.55515 (13)0.10347 (17)0.3934 (3)0.0745 (8)
H39A0.59030.08360.35390.089*
C400.55158 (11)0.09101 (15)0.5233 (3)0.0654 (7)
H40A0.58420.06250.57260.078*
C410.49847 (11)0.12139 (14)0.5828 (2)0.0568 (5)
C420.49593 (11)0.10864 (16)0.7198 (3)0.0615 (5)
N10.21846 (8)0.38865 (11)0.74051 (18)0.0498 (5)
N20.49418 (13)0.09735 (19)0.8305 (3)0.1000 (9)
N30.15370 (15)0.8150 (2)0.7631 (4)0.1453 (15)
N40.16140 (12)0.42632 (19)0.1407 (3)0.0936 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0622 (18)0.0750 (18)0.0733 (19)0.0106 (14)0.0013 (15)0.0096 (14)
C20.0589 (16)0.0502 (14)0.0784 (19)0.0069 (11)−0.0127 (14)0.0018 (13)
C30.087 (2)0.0690 (18)0.085 (2)0.0123 (15)−0.0181 (18)−0.0046 (15)
C40.099 (3)0.074 (2)0.103 (3)0.0135 (18)−0.039 (2)−0.0101 (19)
C50.0617 (19)0.0684 (19)0.147 (3)0.0030 (14)−0.036 (2)−0.016 (2)
C60.0502 (16)0.0723 (18)0.120 (3)−0.0008 (13)−0.0081 (17)−0.0153 (17)
C70.0466 (14)0.0420 (13)0.090 (2)0.0037 (10)−0.0076 (14)−0.0032 (13)
C80.0431 (13)0.0496 (14)0.0794 (18)0.0033 (10)0.0015 (12)−0.0006 (13)
C90.0587 (15)0.0525 (14)0.0719 (18)−0.0067 (11)0.0006 (13)0.0012 (12)
C100.0579 (15)0.0548 (15)0.0735 (17)−0.0081 (11)0.0006 (13)−0.0027 (13)
C110.0484 (14)0.0508 (13)0.0690 (17)0.0086 (11)0.0072 (12)−0.0049 (12)
C120.0631 (17)0.0680 (17)0.081 (2)−0.0004 (13)0.0092 (15)0.0131 (14)
C130.0562 (16)0.0610 (16)0.098 (2)−0.0108 (12)0.0009 (15)0.0044 (15)
C140.0620 (15)0.0597 (15)0.0654 (17)0.0130 (12)0.0105 (13)−0.0061 (12)
C150.0695 (15)0.0446 (13)0.0489 (14)0.0077 (11)0.0013 (12)0.0008 (10)
C160.0570 (14)0.0471 (13)0.0448 (13)0.0072 (10)−0.0003 (11)0.0001 (11)
C170.164 (3)0.0500 (15)0.0443 (15)−0.0021 (17)0.0204 (17)−0.0055 (12)
C180.160 (3)0.0517 (15)0.0433 (15)−0.0013 (17)0.0203 (17)0.0055 (12)
C190.0521 (13)0.0433 (12)0.0455 (13)0.0053 (10)0.0019 (10)−0.0014 (10)
C200.095 (2)0.0570 (15)0.0540 (15)−0.0191 (14)0.0294 (14)−0.0129 (12)
C210.0887 (19)0.0570 (15)0.0497 (15)−0.0178 (13)0.0238 (13)−0.0036 (12)
C220.0552 (14)0.0427 (12)0.0398 (12)0.0043 (10)0.0065 (10)0.0018 (10)
C230.0617 (16)0.0504 (14)0.0714 (17)0.0070 (11)−0.0006 (13)0.0010 (12)
C240.0655 (16)0.0589 (15)0.0668 (17)−0.0075 (12)−0.0024 (13)−0.0009 (13)
C250.0798 (18)0.0471 (13)0.0539 (15)−0.0019 (13)0.0085 (13)−0.0008 (11)
C260.0755 (18)0.0463 (14)0.0756 (18)0.0130 (12)0.0075 (15)0.0111 (12)
C270.0554 (14)0.0511 (14)0.0593 (15)0.0034 (11)−0.0005 (12)0.0082 (11)
C280.072 (2)0.0641 (17)0.122 (3)0.0005 (15)−0.0199 (19)0.0240 (17)
C290.0571 (14)0.0423 (12)0.0657 (16)0.0014 (10)0.0088 (12)−0.0032 (11)
C300.0530 (13)0.0381 (11)0.0450 (12)−0.0003 (9)0.0009 (10)−0.0029 (10)
C310.0697 (16)0.0384 (12)0.0647 (16)0.0147 (11)0.0157 (13)0.0077 (11)
C320.0686 (16)0.0444 (13)0.0602 (15)0.0089 (11)0.0152 (12)0.0098 (11)
C330.0513 (13)0.0408 (12)0.0432 (12)0.0048 (9)−0.0032 (10)−0.0014 (10)
C340.0523 (13)0.0342 (11)0.0538 (14)0.0033 (9)−0.0034 (11)0.0021 (10)
C350.0535 (13)0.0385 (11)0.0496 (13)−0.0032 (10)0.0018 (10)0.0026 (10)
C360.0501 (13)0.0379 (11)0.0556 (14)0.0018 (9)0.0020 (11)−0.0032 (10)
C370.0677 (16)0.0667 (16)0.0630 (17)0.0152 (13)0.0139 (13)0.0042 (13)
C380.082 (2)0.0767 (19)0.082 (2)0.0141 (16)0.0280 (17)0.0019 (15)
C390.0667 (18)0.0627 (17)0.097 (2)0.0042 (13)0.0250 (17)−0.0140 (16)
C400.0468 (14)0.0489 (14)0.099 (2)0.0018 (10)−0.0033 (14)−0.0088 (14)
C410.0529 (11)0.0468 (10)0.0684 (12)0.0022 (9)−0.0103 (11)−0.0051 (10)
C420.0559 (11)0.0533 (11)0.0723 (13)0.0054 (9)−0.0128 (11)−0.0034 (11)
N10.0548 (11)0.0409 (10)0.0530 (11)0.0087 (8)0.0009 (9)−0.0067 (8)
N20.093 (2)0.125 (2)0.0771 (19)0.0226 (15)−0.0209 (15)0.0079 (16)
N30.086 (2)0.113 (2)0.225 (4)−0.0195 (17)−0.059 (2)0.054 (2)
N40.0671 (17)0.121 (2)0.094 (2)0.0082 (15)0.0118 (15)0.0107 (16)
Geometric parameters (Å, °) top
C1—N41.138 (3)C21—H21A0.9300
C1—C21.432 (4)C22—C231.381 (3)
C2—C31.386 (4)C22—C271.399 (3)
C2—C71.406 (4)C23—C241.381 (3)
C3—C41.363 (4)C23—H23A0.9300
C3—H3A0.9300C24—C251.364 (3)
C4—C51.368 (5)C24—H24A0.9300
C4—H4A0.9300C25—C261.365 (3)
C5—C61.390 (4)C25—H25A0.9300
C5—H5A0.9300C26—C271.384 (3)
C6—C71.399 (3)C26—H26A0.9300
C6—H6A0.9300C27—C281.424 (4)
C7—C81.485 (4)C28—N31.139 (4)
C8—C131.382 (4)C29—N11.463 (3)
C8—C91.394 (3)C29—C301.504 (3)
C9—C101.369 (3)C29—H29A0.9700
C9—H9A0.9300C29—H29B0.9700
C10—C111.383 (3)C30—C351.380 (3)
C10—H10A0.9300C30—C311.380 (3)
C11—C121.379 (3)C31—C321.379 (3)
C11—C141.501 (3)C31—H31A0.9300
C12—C131.379 (4)C32—C331.394 (3)
C12—H12A0.9300C32—H32A0.9300
C13—H13A0.9300C33—C341.388 (3)
C14—N11.473 (3)C33—C361.480 (3)
C14—H14A0.9700C34—C351.376 (3)
C14—H14B0.9700C34—H34A0.9300
C15—N11.468 (3)C35—H35A0.9300
C15—C161.505 (3)C36—C371.380 (3)
C15—H15A0.9700C36—C411.394 (3)
C15—H15B0.9700C37—C381.377 (3)
C16—C211.365 (3)C37—H37A0.9300
C16—C171.374 (3)C38—C391.364 (4)
C17—C181.379 (3)C38—H38A0.9300
C17—H17A0.9300C39—C401.358 (4)
C18—C191.373 (3)C39—H39A0.9300
C18—H18A0.9300C40—C411.405 (3)
C19—C201.361 (3)C40—H40A0.9300
C19—C221.490 (3)C41—C421.429 (4)
C20—C211.380 (3)C42—N21.156 (3)
C20—H20A0.9300
N4—C1—C2179.0 (3)C20—C21—H21A119.5
C3—C2—C7120.9 (3)C23—C22—C27116.7 (2)
C3—C2—C1117.4 (3)C23—C22—C19121.39 (19)
C7—C2—C1121.7 (2)C27—C22—C19121.9 (2)
C4—C3—C2121.1 (3)C24—C23—C22121.9 (2)
C4—C3—H3A119.5C24—C23—H23A119.0
C2—C3—H3A119.5C22—C23—H23A119.0
C3—C4—C5119.0 (3)C25—C24—C23120.1 (2)
C3—C4—H4A120.5C25—C24—H24A119.9
C5—C4—H4A120.5C23—C24—H24A119.9
C4—C5—C6121.7 (3)C24—C25—C26119.8 (2)
C4—C5—H5A119.2C24—C25—H25A120.1
C6—C5—H5A119.2C26—C25—H25A120.1
C5—C6—C7120.2 (3)C25—C26—C27120.3 (2)
C5—C6—H6A119.9C25—C26—H26A119.9
C7—C6—H6A119.9C27—C26—H26A119.9
C6—C7—C2117.2 (3)C26—C27—C22121.1 (2)
C6—C7—C8120.3 (3)C26—C27—C28119.1 (2)
C2—C7—C8122.5 (2)C22—C27—C28119.7 (2)
C13—C8—C9116.9 (2)N3—C28—C27177.1 (3)
C13—C8—C7121.1 (2)N1—C29—C30113.78 (18)
C9—C8—C7121.9 (2)N1—C29—H29A108.8
C10—C9—C8121.1 (2)C30—C29—H29A108.8
C10—C9—H9A119.5N1—C29—H29B108.8
C8—C9—H9A119.5C30—C29—H29B108.8
C9—C10—C11121.8 (2)H29A—C29—H29B107.7
C9—C10—H10A119.1C35—C30—C31117.6 (2)
C11—C10—H10A119.1C35—C30—C29120.0 (2)
C12—C11—C10117.3 (2)C31—C30—C29122.31 (19)
C12—C11—C14122.1 (2)C32—C31—C30121.8 (2)
C10—C11—C14120.5 (2)C32—C31—H31A119.1
C13—C12—C11121.0 (3)C30—C31—H31A119.1
C13—C12—H12A119.5C31—C32—C33120.4 (2)
C11—C12—H12A119.5C31—C32—H32A119.8
C12—C13—C8121.8 (2)C33—C32—H32A119.8
C12—C13—H13A119.1C34—C33—C32117.8 (2)
C8—C13—H13A119.1C34—C33—C36122.11 (19)
N1—C14—C11111.64 (19)C32—C33—C36120.1 (2)
N1—C14—H14A109.3C35—C34—C33120.90 (19)
C11—C14—H14A109.3C35—C34—H34A119.6
N1—C14—H14B109.3C33—C34—H34A119.6
C11—C14—H14B109.3C34—C35—C30121.6 (2)
H14A—C14—H14B108.0C34—C35—H35A119.2
N1—C15—C16112.73 (17)C30—C35—H35A119.2
N1—C15—H15A109.0C37—C36—C41117.1 (2)
C16—C15—H15A109.0C37—C36—C33119.8 (2)
N1—C15—H15B109.0C41—C36—C33123.1 (2)
C16—C15—H15B109.0C38—C37—C36121.8 (3)
H15A—C15—H15B107.8C38—C37—H37A119.1
C21—C16—C17117.1 (2)C36—C37—H37A119.1
C21—C16—C15121.6 (2)C39—C38—C37120.4 (3)
C17—C16—C15121.3 (2)C39—C38—H38A119.8
C16—C17—C18121.8 (2)C37—C38—H38A119.8
C16—C17—H17A119.1C40—C39—C38120.2 (3)
C18—C17—H17A119.1C40—C39—H39A119.9
C19—C18—C17120.6 (2)C38—C39—H39A119.9
C19—C18—H18A119.7C39—C40—C41119.8 (2)
C17—C18—H18A119.7C39—C40—H40A120.1
C20—C19—C18117.5 (2)C41—C40—H40A120.1
C20—C19—C22121.6 (2)C36—C41—C40120.8 (2)
C18—C19—C22120.8 (2)C36—C41—C42120.2 (2)
C19—C20—C21121.8 (2)C40—C41—C42118.9 (2)
C19—C20—H20A119.1N2—C42—C41179.2 (3)
C21—C20—H20A119.1C29—N1—C15111.04 (17)
C16—C21—C20121.1 (2)C29—N1—C14109.79 (17)
C16—C21—H21A119.5C15—N1—C14110.46 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N3i0.932.553.446 (5)162.
C24—H24A···N2ii0.932.593.350 (4)139.
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···N3i0.932.553.446 (5)162.
C24—H24A···N2ii0.932.593.350 (4)139.
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+2.
Acknowledgements top

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

references
References top

Chen, Q., Buss, C. E., Young, V. G. Jr & Fox, S. (2005). J. Chem. Crystallogr. 35, 177–181.

Foces-Foces, C., Llamas-Saiz, A. L., Alajarín, M., López-Lázaro, A. & Molina, P. (1999). Acta Cryst. C55, 373–377.

Fox, S., Nanthakumar, A., Wikström, M., Karlin, K. D. & Blackburn, N. J. (1996). J. Am. Chem. Soc. 118, 24–34.

Iwasaki, F. & Iwasaki, H. (1972). Acta Cryst. B28, 3370–3376.

Menage, S., Zang, Y., Hendrich, M. P. & Que, L. Jr (1992). J. Am. Chem. Soc. 114, 7786–7792.

Murthy, N. N. & Karlin, K. D. (1993). J. Am. Chem. Soc. 115, 1236–1238.

Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.

Schrock, R. R. (1997). Acc. Chem. Res. 30, 9–16.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.