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Acta Cryst. (2007). E63, o3937    [ doi:10.1107/S1600536807041943 ]

4-{[6-(4,4'-Bipyridin-1-ium-1-yl)-2-(4-carboxyanilino)-1,3,5-triazin-2-yl]amino}benzoate monohydrate

J. Chen and Y. Ruan

Abstract top

Reaction of 2,4,6-tris(4-carboxyanilino)-1,3,5-triazine with 4,4'-bipyridine yields the zwitterionic title compound, C27H19N7O4·H2O. The zwitterionic form is confirmed by the the C-O distances of the carboxylate group. The crystal structure involves intermolecular N-H...O, O-H...O and O-H...N hydrogen bonds.

Comment top

It is well known that chlorine atoms in cyanuric chloride are easily replaced by other organic groups (Thurston et al., 1951). Using cyanuric chloride as reactant and controlling stoichiometry and reaction temperature, we have synthesized a new triazine derivative, 2-[(4-carboxylatephenyl)amino]-4-[(4-carboxyphenyl)amino]- 6-(4,4'-bipyridin-1-yl)-1,3,5-triazine (Fig. 3). The title organic compound exists as a zwitterion. Some highly related zwitterionic triazine derivatives have been published by some patents (Sahouani, 2006; Sahouani & Vogel, 2002; Sahouani, Vogel & Schaberg, 2002; Sahouani et al., 2001). Nevertheless, to the best of our knowledge, no crystal data are known for zwitterionic triazines (Cambridge Structural Database, Version 5.28 of May 2007; Allen, 2002).

The title compound was synthesized by treating 2,4,6-tri((4-carboxyphenyl) amino)-1,3,5-triazine and 4,4'-bipy in DMF solution. In the title organic compound, as shown in figure 1, the 6-position of triazine ring is occupied by the cationic 4,4'-bipyridin-1-yl group and whereas the anionic (4-carboxylatephenyl)amino substituent is observed in the 2-position, making the title compound a zwitterion. The zwitteric character is also confirmed by the C—O distances of the carboxylate and carboxy group. The double bond C=O (C4—O1: 1.201 (2) Å) in the carboxy moiety is clearly shorter than the single bond C—O (C4—O2: 1.299 (2) Å) and the nearly equivalent distances of C5—O3(1.251 (2) Å) and C5—O4 (1.262 (2) Å) vertify the anionic nature of the carboxylate function in the 2-position of triazine ring. The torsional angles [C14—C13—C21—C25] and [C12—C13—C21—C22] are 19.5 (3)° and 17.3 (3)°, respectively, confirming that the two pyridine subunits of the 4,4-bipy are not coplanar. The H atoms of water molecule, N—H group and carboxy build up an intricated H-bond network with O and N atoms (figure 2).

Related literature top

For related literature, see: Sahouani (2006); Sahouani & Vogel (2002); Sahouani, Vogel & Schaberg (2002); Sahouani et al. (2001); Thurston et al. (1951); Allen (2002).

Experimental top

2,4,6-tri((4-carboxyphenyl)amino)-1,3,5-triazine: 4.6 g (0.025 mol) cyanuric chloride reacted with 21.3 g (0.155 mol) p-aminobenzoic acid in 250 ml acetone at 45° for 12 h creating a substantive white deposit. After cooling, the white product was filtered from the reaction mixture, washed free of hydrochloric acid salt of p-aminobenzoic acid with water and oven-dried at 60° (76% yield).

2-((4-carboxylatephenyl)amino)-4-((4-carboxyphenyl)amino) −6-(4,4'-bipyridin-1-yl)-1,3,5-triazine: 9.7 g (0.02 mol) 2,4,6-tri ((4-carboxyphenyl)amino)-1,3,5-triazine reacted with 3.1 g (0.02 mol) 4,4-bipy in 150 ml DMF at 100° for 8 h creating an orange–yellow deposit. After cooling, the orange–yellow product was filtered from the reaction mixture, washed free of impurity with DMF and acetone and oven-dried at 60° (95% yield). A solution of 0.15 g product and 25 ml H2O was heated in an autoclave at 160° for 1 days and then cooled to room temperature for 3 days, creating the red crystal of the title compound.

Refinement top

Anisotropic thermal parameters were applied to all non-hydrogen atoms. All hydrogen atoms were located in a difference map and refined isotropically. All calculations were performed with SHELXL97 program package (Sheldrick, 1997).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2000); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2000); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Molecular Structure Corporation & Rigaku, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. ORTEP drawing of the title compound with thermal ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. Crystal structure of the title compound with hydrogen bonds indicated as dashed lines. Hydrogen atoms not taking part in hydrogen bonds are omitted for the sake of clarity.
[Figure 3] Fig. 3. The formation of the title compound.
4-{[6-(4,4'-Bipyridin-1-ium-1-yl)-2-(4-carboxyanilino)-1,3,5-triazin- 2-yl]amino}benzoate monohydrate top
Crystal data top
C27H19N7O4·H2OZ = 2
Mr = 523.51F000 = 544
Triclinic, P1Dx = 1.473 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.500 (5) ÅCell parameters from 2378 reflections
b = 9.523 (5) Åθ = 3.1–27.5º
c = 13.669 (7) ŵ = 0.11 mm−1
α = 97.527 (3)ºT = 293 (2) K
β = 98.781 (6)ºPrism, red
γ = 101.555 (6)º0.78 × 0.20 × 0.05 mm
V = 1181 (1) Å3
Data collection top
Rigaku Mercury CCD
diffractometer		5350 independent reflections
Radiation source: rotating-anode generator3866 reflections with I > 2σ(I)
Monochromator: Graphite MonochromatorRint = 0.025
T = 130.1500 Kθmax = 27.5º
ω scansθmin = 3.1º
Absorption correction: multi-scan
(SPHERE in CrystalStructure; Molecular Structure Corporation & Rigaku, 2000)		h = −12→10
Tmin = 0.975, Tmax = 0.995k = −12→12
9219 measured reflectionsl = −17→17
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052All H-atom parameters refined
wR(F2) = 0.161  w = 1/[σ2(Fo2) + (0.0989P)2 + 0.007P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
5350 reflectionsΔρmax = 0.24 e Å−3
436 parametersΔρmin = −0.22 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C27H19N7O4·H2Oγ = 101.555 (6)º
Mr = 523.51V = 1181 (1) Å3
Triclinic, P1Z = 2
a = 9.500 (5) ÅMo Kα
b = 9.523 (5) ŵ = 0.11 mm−1
c = 13.669 (7) ÅT = 293 (2) K
α = 97.527 (3)º0.78 × 0.20 × 0.05 mm
β = 98.781 (6)º
Data collection top
Rigaku Mercury CCD
diffractometer		5350 independent reflections
Absorption correction: multi-scan
(SPHERE in CrystalStructure; Molecular Structure Corporation & Rigaku, 2000)		3866 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.995Rint = 0.025
9219 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052436 parameters
wR(F2) = 0.161All H-atom parameters refined
S = 1.00Δρmax = 0.24 e Å−3
5350 reflectionsΔρmin = −0.22 e Å−3
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 > 2sigma(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
C10.03809 (18)0.35605 (19)0.58550 (13)0.0311 (4)
C20.08201 (19)0.2646 (2)0.43911 (13)0.0327 (4)
C30.20747 (18)0.48675 (19)0.51904 (12)0.0299 (4)
C40.2237 (2)0.1994 (2)−0.01844 (14)0.0393 (4)
C50.73347 (19)0.8236 (2)0.29767 (13)0.0348 (4)
C11−0.0278 (2)0.4560 (2)0.74022 (16)0.0432 (5)
H110.041 (3)0.541 (3)0.7332 (18)0.060 (7)*
C12−0.0998 (2)0.4443 (2)0.81892 (16)0.0461 (5)
H12−0.081 (2)0.528 (3)0.8678 (18)0.054 (6)*
C13−0.1926 (2)0.3146 (2)0.82586 (14)0.0366 (4)
C14−0.2132 (2)0.2012 (2)0.74647 (16)0.0442 (5)
H14−0.281 (2)0.111 (3)0.7402 (16)0.048 (6)*
C15−0.1397 (2)0.2162 (2)0.66821 (16)0.0417 (4)
H15−0.145 (3)0.142 (3)0.6113 (18)0.058 (7)*
C21−0.2584 (2)0.2992 (2)0.91672 (14)0.0396 (4)
C22−0.2628 (3)0.4192 (3)0.9843 (2)0.0690 (8)
H22−0.242 (4)0.514 (4)0.967 (3)0.107 (11)*
C23−0.3071 (3)0.4008 (3)1.0745 (2)0.0700 (8)
H23−0.312 (3)0.481 (4)1.127 (2)0.090 (9)*
C24−0.3487 (2)0.1571 (3)1.03494 (16)0.0474 (5)
H24−0.378 (3)0.060 (3)1.053 (2)0.079 (8)*
C25−0.3074 (2)0.1647 (2)0.94255 (15)0.0424 (5)
H25−0.314 (2)0.073 (3)0.8954 (17)0.052 (6)*
C310.0955 (2)0.17036 (18)0.26628 (13)0.0334 (4)
C32−0.0094 (2)0.1463 (2)0.18007 (14)0.0405 (4)
H32−0.114 (3)0.123 (2)0.1836 (17)0.053 (6)*
C330.0321 (2)0.1576 (2)0.08816 (15)0.0410 (4)
H33−0.042 (2)0.138 (2)0.0292 (16)0.043 (5)*
C340.1787 (2)0.19018 (19)0.08102 (13)0.0341 (4)
C350.2832 (2)0.2111 (2)0.16743 (15)0.0385 (4)
H350.385 (3)0.232 (2)0.1634 (17)0.052 (6)*
C360.2429 (2)0.2014 (2)0.25980 (14)0.0381 (4)
H360.319 (2)0.219 (2)0.3164 (16)0.042 (5)*
C410.40884 (18)0.65630 (18)0.46672 (13)0.0304 (4)
C420.4296 (2)0.5703 (2)0.38177 (14)0.0379 (4)
H420.372 (2)0.476 (2)0.3605 (16)0.045 (6)*
C430.5345 (2)0.6248 (2)0.32829 (14)0.0375 (4)
H430.547 (3)0.561 (3)0.2705 (19)0.058 (7)*
C440.61918 (18)0.76485 (19)0.35593 (13)0.0322 (4)
C450.5971 (2)0.8504 (2)0.44022 (14)0.0378 (4)
H450.659 (2)0.954 (3)0.4624 (17)0.050 (6)*
C460.4942 (2)0.7971 (2)0.49517 (14)0.0366 (4)
H460.479 (2)0.855 (2)0.5542 (16)0.043 (6)*
N10.00548 (16)0.24207 (17)0.51393 (11)0.0352 (3)
N20.18480 (16)0.38337 (16)0.43910 (11)0.0330 (3)
N30.13091 (16)0.48030 (16)0.59582 (11)0.0338 (3)
N4−0.04689 (16)0.34248 (16)0.66637 (11)0.0328 (3)
N5−0.3460 (2)0.2723 (2)1.10135 (13)0.0534 (5)
N60.04740 (19)0.15736 (18)0.35875 (12)0.0401 (4)
H6−0.039 (3)0.092 (3)0.3552 (19)0.065 (8)*
N70.30777 (16)0.61188 (17)0.52825 (12)0.0338 (3)
H70.314 (2)0.673 (2)0.5862 (17)0.042 (6)*
O10.34478 (19)0.1932 (3)−0.03132 (13)0.0833 (7)
O20.12177 (15)0.21458 (18)−0.08863 (11)0.0496 (4)
H30.160 (4)0.229 (4)−0.159 (3)0.108 (11)*
O30.77794 (16)0.95853 (16)0.30828 (12)0.0505 (4)
O40.77886 (16)0.73177 (16)0.24276 (10)0.0455 (4)
O50.6274 (2)1.1778 (2)0.29330 (13)0.0610 (5)
H10.640 (3)1.213 (3)0.239 (2)0.072 (8)*
H20.677 (4)1.116 (4)0.302 (3)0.106 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0306 (9)0.0380 (9)0.0294 (8)0.0086 (7)0.0126 (7)0.0133 (7)
C20.0323 (9)0.0368 (9)0.0299 (8)0.0055 (7)0.0091 (7)0.0084 (7)
C30.0294 (8)0.0334 (9)0.0303 (8)0.0077 (7)0.0101 (7)0.0108 (7)
C40.0406 (10)0.0429 (11)0.0379 (10)0.0118 (8)0.0144 (8)0.0070 (8)
C50.0307 (9)0.0410 (10)0.0336 (9)0.0034 (7)0.0087 (7)0.0138 (8)
C110.0543 (12)0.0339 (10)0.0435 (11)0.0040 (9)0.0225 (9)0.0073 (9)
C120.0621 (13)0.0354 (10)0.0427 (11)0.0048 (9)0.0259 (10)0.0044 (9)
C130.0410 (10)0.0377 (10)0.0367 (9)0.0118 (8)0.0159 (8)0.0119 (8)
C140.0506 (12)0.0396 (10)0.0428 (11)0.0001 (9)0.0215 (9)0.0084 (9)
C150.0478 (11)0.0379 (10)0.0388 (10)0.0003 (8)0.0190 (9)0.0055 (8)
C210.0441 (11)0.0419 (10)0.0373 (10)0.0096 (8)0.0186 (8)0.0098 (8)
C220.110 (2)0.0455 (13)0.0607 (15)0.0097 (13)0.0539 (15)0.0101 (12)
C230.097 (2)0.0574 (15)0.0566 (15)0.0019 (14)0.0446 (15)−0.0007 (12)
C240.0440 (11)0.0574 (13)0.0426 (11)0.0045 (10)0.0142 (9)0.0187 (10)
C250.0437 (11)0.0433 (11)0.0410 (10)0.0053 (9)0.0141 (9)0.0099 (9)
C310.0401 (10)0.0292 (9)0.0299 (8)0.0009 (7)0.0132 (7)0.0044 (7)
C320.0338 (10)0.0497 (11)0.0360 (10)0.0009 (8)0.0112 (8)0.0071 (9)
C330.0374 (10)0.0520 (12)0.0333 (9)0.0067 (9)0.0089 (8)0.0085 (8)
C340.0394 (10)0.0315 (9)0.0335 (9)0.0084 (7)0.0126 (8)0.0054 (7)
C350.0343 (10)0.0427 (10)0.0399 (10)0.0073 (8)0.0134 (8)0.0059 (8)
C360.0369 (10)0.0440 (10)0.0321 (9)0.0070 (8)0.0071 (8)0.0032 (8)
C410.0305 (8)0.0311 (8)0.0326 (8)0.0065 (7)0.0108 (7)0.0103 (7)
C420.0417 (10)0.0317 (9)0.0386 (10)−0.0003 (8)0.0167 (8)0.0028 (8)
C430.0421 (10)0.0356 (10)0.0349 (9)0.0027 (8)0.0171 (8)0.0036 (8)
C440.0308 (9)0.0348 (9)0.0324 (9)0.0042 (7)0.0094 (7)0.0111 (7)
C450.0420 (10)0.0319 (9)0.0368 (9)−0.0003 (8)0.0127 (8)0.0040 (8)
C460.0437 (10)0.0351 (9)0.0309 (9)0.0050 (8)0.0145 (8)0.0021 (7)
N10.0356 (8)0.0398 (8)0.0315 (7)0.0038 (6)0.0127 (6)0.0098 (7)
N20.0338 (8)0.0358 (8)0.0295 (7)0.0029 (6)0.0108 (6)0.0071 (6)
N30.0363 (8)0.0359 (8)0.0319 (7)0.0068 (6)0.0136 (6)0.0089 (6)
N40.0352 (8)0.0374 (8)0.0292 (7)0.0079 (6)0.0128 (6)0.0102 (6)
N50.0499 (10)0.0721 (13)0.0376 (9)0.0039 (9)0.0175 (8)0.0113 (9)
N60.0431 (9)0.0397 (9)0.0327 (8)−0.0052 (7)0.0138 (7)0.0026 (7)
N70.0394 (8)0.0331 (8)0.0304 (7)0.0044 (6)0.0157 (6)0.0055 (6)
O10.0547 (10)0.165 (2)0.0506 (10)0.0497 (12)0.0267 (8)0.0323 (12)
O20.0458 (8)0.0701 (10)0.0386 (8)0.0144 (7)0.0163 (6)0.0179 (7)
O30.0485 (8)0.0426 (8)0.0592 (9)−0.0049 (6)0.0213 (7)0.0139 (7)
O40.0533 (8)0.0507 (8)0.0432 (7)0.0160 (7)0.0264 (7)0.0190 (7)
O50.0852 (13)0.0693 (11)0.0385 (9)0.0276 (10)0.0260 (8)0.0119 (8)
Geometric parameters (Å, °) top
C1—N31.303 (2)C24—N51.323 (3)
C1—N11.314 (2)C24—C251.385 (3)
C1—N41.469 (2)C24—H240.99 (3)
C2—N21.338 (2)C25—H251.00 (2)
C2—N61.349 (2)C31—C321.384 (3)
C2—N11.357 (2)C31—C361.390 (3)
C3—N21.331 (2)C31—N61.420 (2)
C3—N71.346 (2)C32—C331.384 (3)
C3—N31.366 (2)C32—H320.99 (2)
C4—O11.201 (2)C33—C341.386 (3)
C4—O21.299 (2)C33—H330.96 (2)
C4—C341.494 (3)C34—C351.386 (3)
C5—O31.251 (2)C35—C361.383 (3)
C5—O41.262 (2)C35—H350.96 (2)
C5—C441.505 (2)C36—H360.95 (2)
C11—N41.342 (3)C41—C461.392 (3)
C11—C121.365 (3)C41—C421.394 (3)
C11—H110.96 (3)C41—N71.409 (2)
C12—C131.390 (3)C42—C431.383 (3)
C12—H120.94 (2)C42—H420.93 (2)
C13—C141.388 (3)C43—C441.383 (3)
C13—C211.484 (3)C43—H430.96 (2)
C14—C151.371 (3)C44—C451.390 (3)
C14—H140.95 (2)C45—C461.379 (3)
C15—N41.347 (2)C45—H451.02 (2)
C15—H150.97 (2)C46—H460.96 (2)
C21—C251.382 (3)N6—H60.92 (3)
C21—C221.384 (3)N7—H70.90 (2)
C22—C231.383 (3)O2—H31.09 (4)
C22—H220.96 (4)O5—H10.87 (3)
C23—N51.321 (3)O5—H20.84 (4)
C23—H230.99 (3)
N3—C1—N1130.88 (16)C31—C32—C33120.11 (18)
N3—C1—N4114.54 (15)C31—C32—H32120.5 (13)
N1—C1—N4114.56 (15)C33—C32—H32119.4 (13)
N2—C2—N6119.02 (16)C32—C33—C34120.60 (18)
N2—C2—N1125.34 (16)C32—C33—H33118.9 (13)
N6—C2—N1115.63 (16)C34—C33—H33120.4 (13)
N2—C3—N7121.14 (15)C33—C34—C35118.96 (17)
N2—C3—N3124.74 (16)C33—C34—C4120.67 (17)
N7—C3—N3114.07 (15)C35—C34—C4120.36 (16)
O1—C4—O2123.42 (19)C36—C35—C34120.89 (18)
O1—C4—C34122.06 (18)C36—C35—H35119.3 (14)
O2—C4—C34114.52 (16)C34—C35—H35119.8 (14)
O3—C5—O4125.01 (17)C35—C36—C31119.67 (17)
O3—C5—C44118.09 (17)C35—C36—H36117.2 (13)
O4—C5—C44116.89 (17)C31—C36—H36123.1 (13)
N4—C11—C12120.54 (19)C46—C41—C42118.70 (16)
N4—C11—H11114.6 (15)C46—C41—N7116.19 (15)
C12—C11—H11124.9 (15)C42—C41—N7125.12 (16)
C11—C12—C13121.24 (19)C43—C42—C41119.96 (17)
C11—C12—H12115.6 (15)C43—C42—H42119.8 (13)
C13—C12—H12123.2 (15)C41—C42—H42120.2 (13)
C14—C13—C12116.49 (18)C42—C43—C44121.60 (17)
C14—C13—C21122.90 (18)C42—C43—H43117.4 (15)
C12—C13—C21120.54 (18)C44—C43—H43121.0 (15)
C15—C14—C13120.92 (19)C43—C44—C45118.13 (16)
C15—C14—H14115.3 (14)C43—C44—C5121.43 (16)
C13—C14—H14123.7 (14)C45—C44—C5120.44 (17)
N4—C15—C14120.50 (18)C46—C45—C44121.02 (18)
N4—C15—H15113.3 (15)C46—C45—H45119.5 (13)
C14—C15—H15126.2 (15)C44—C45—H45119.5 (13)
C25—C21—C22116.44 (19)C45—C46—C41120.59 (17)
C25—C21—C13121.78 (18)C45—C46—H46121.7 (13)
C22—C21—C13121.57 (19)C41—C46—H46117.7 (13)
C23—C22—C21119.9 (2)C1—N1—C2111.57 (15)
C23—C22—H22120 (2)C3—N2—C2115.17 (15)
C21—C22—H22120 (2)C1—N3—C3112.10 (15)
N5—C23—C22123.4 (2)C11—N4—C15120.22 (16)
N5—C23—H23112.3 (19)C11—N4—C1119.24 (16)
C22—C23—H23124.4 (19)C15—N4—C1120.50 (15)
N5—C24—C25123.8 (2)C23—N5—C24116.8 (2)
N5—C24—H24118.4 (16)C2—N6—C31124.14 (16)
C25—C24—H24117.7 (17)C2—N6—H6114.7 (16)
C21—C25—C24119.4 (2)C31—N6—H6116.0 (16)
C21—C25—H25121.0 (13)C3—N7—C41130.48 (15)
C24—C25—H25119.6 (13)C3—N7—H7112.8 (14)
C32—C31—C36119.75 (17)C41—N7—H7116.5 (14)
C32—C31—N6117.98 (16)C4—O2—H3113.1 (17)
C36—C31—N6122.24 (16)H1—O5—H2111 (3)
N4—C11—C12—C131.1 (3)O3—C5—C44—C45−19.6 (3)
C11—C12—C13—C14−3.2 (3)O4—C5—C44—C45159.23 (17)
C11—C12—C13—C21173.84 (19)C43—C44—C45—C460.4 (3)
C12—C13—C14—C153.0 (3)C5—C44—C45—C46−179.00 (17)
C21—C13—C14—C15−173.97 (19)C44—C45—C46—C41−0.7 (3)
C13—C14—C15—N4−0.7 (3)C42—C41—C46—C450.1 (3)
C14—C13—C21—C2519.5 (3)N7—C41—C46—C45179.55 (16)
C12—C13—C21—C25−157.3 (2)N3—C1—N1—C2−1.7 (3)
C14—C13—C21—C22−165.9 (2)N4—C1—N1—C2176.68 (13)
C12—C13—C21—C2217.3 (3)N2—C2—N1—C13.8 (3)
C25—C21—C22—C233.4 (4)N6—C2—N1—C1−175.18 (16)
C13—C21—C22—C23−171.5 (2)N7—C3—N2—C2−179.89 (16)
C21—C22—C23—N50.4 (5)N3—C3—N2—C2−2.4 (2)
C22—C21—C25—C24−3.9 (3)N6—C2—N2—C3176.99 (16)
C13—C21—C25—C24170.90 (18)N1—C2—N2—C3−2.0 (3)
N5—C24—C25—C210.9 (3)N1—C1—N3—C3−2.0 (3)
C36—C31—C32—C33−2.0 (3)N4—C1—N3—C3179.63 (13)
N6—C31—C32—C33−179.95 (17)N2—C3—N3—C14.2 (2)
C31—C32—C33—C341.3 (3)N7—C3—N3—C1−178.17 (15)
C32—C33—C34—C350.1 (3)C12—C11—N4—C151.2 (3)
C32—C33—C34—C4178.73 (18)C12—C11—N4—C1−176.76 (18)
O1—C4—C34—C33−162.1 (2)C14—C15—N4—C11−1.4 (3)
O2—C4—C34—C3317.9 (3)C14—C15—N4—C1176.54 (17)
O1—C4—C34—C3516.4 (3)N3—C1—N4—C112.3 (2)
O2—C4—C34—C35−163.47 (18)N1—C1—N4—C11−176.29 (16)
C33—C34—C35—C36−0.7 (3)N3—C1—N4—C15−175.66 (17)
C4—C34—C35—C36−179.34 (17)N1—C1—N4—C155.7 (2)
C34—C35—C36—C310.0 (3)C22—C23—N5—C24−3.5 (4)
C32—C31—C36—C351.4 (3)C25—C24—N5—C232.9 (3)
N6—C31—C36—C35179.24 (17)N2—C2—N6—C31−10.6 (3)
C46—C41—C42—C430.7 (3)N1—C2—N6—C31168.53 (16)
N7—C41—C42—C43−178.65 (17)C32—C31—N6—C2−122.3 (2)
C41—C42—C43—C44−1.0 (3)C36—C31—N6—C259.8 (3)
C42—C43—C44—C450.5 (3)N2—C3—N7—C41−4.3 (3)
C42—C43—C44—C5179.85 (17)N3—C3—N7—C41177.97 (16)
O3—C5—C44—C43161.03 (18)C46—C41—N7—C3177.20 (17)
O4—C5—C44—C43−20.1 (3)C42—C41—N7—C3−3.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O3i0.92 (3)1.90 (3)2.791 (2)164 (2)
N7—H7···O5ii0.90 (2)1.96 (2)2.847 (3)167 (2)
O2—H3···O4iii1.09 (4)1.42 (4)2.507 (2)172 (3)
O5—H1···N5iv0.87 (3)2.05 (3)2.914 (3)173 (3)
O5—H2···O30.84 (4)1.94 (4)2.769 (3)173 (4)
Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z; (iv) x+1, y+1, z−1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O3i0.92 (3)1.90 (3)2.791 (2)164 (2)
N7—H7···O5ii0.90 (2)1.96 (2)2.847 (3)167 (2)
O2—H3···O4iii1.09 (4)1.42 (4)2.507 (2)172 (3)
O5—H1···N5iv0.87 (3)2.05 (3)2.914 (3)173 (3)
O5—H2···O30.84 (4)1.94 (4)2.769 (3)173 (4)
Symmetry codes: (i) x−1, y−1, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z; (iv) x+1, y+1, z−1.
Acknowledgements top

The authors gratefully acknowledge the financial support of the Key Science and Technology Project of Fujian Province (grant No. 2005H045)

references
References top

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