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Acta Cryst. (2007). E63, m1583    [ doi:10.1107/S160053680702034X ]

Bis(2,3,5-triphenyltetrazolium) tetrachloridocadmate(II)

S.-F. Zhang, X.-G. Yang, Z. Liu, W.-H. Li and B.-R. Hou

Abstract top

The title compound, (C19H15N4)2[CdCl4], a salt comprising two 2,3,5-triphenyl-substituted tetrazolium cations and a tetrachloridocadmate(II) anion, was synthesized by hydrothermal methods. In the anion, the CdII ion is tetrahedrally coordinated by four chloride anions. In the crystal structure, four cations and two anions pack into inversion-related subunits linked by C-H...Cl and offset [pi]-stacking interactions. Each of these subunits is surrounded by six others. Intermolecular [pi]-[pi] stacking interactions between phenyl rings are observed along the a axis, with perpendicular distances between the ring planes of 3.6015 and 3.6934 Å.

Comment top

Tetrazole derivatives are frequently used as colour indicators for the detection of enzyme systems in which reduction equivalents are formed. Due to this feature, they are extremely useful tools in academic and clinical research as well as for many diagnostic applications (Benon et al., 1980). The tetrazole derivatives most used in biochemistry and cell biology are aromatic derivatives of 1,2,3,4-tetrazole (substitution at positions 2, 3, and 5). So far 2, 3, 5-triphenyl-2H-tetrazolium salts have received a great deal of attention (Předota et al., 1991). Here we report the crystal structure of the title compound a 2,3,5-triphenyl-2H-tetrazolium salt.

The title compound (C19H15N4)2.(CdCl4), a salt comprising two 2,3,5-triphenylsubstituted tetrazolium cations and a tetrachloridocadmate anion (Fig. 1) was synthesized by hydrothermal methods. Bond lengths and angles in the tetrazole unit, Table 1, are in good agreement with those reported previously (Morsy et al., 2007). In the [(CdCl4)2-] anion, the Cd (II) ion is tetra-coordinated by four chloride atoms, with the bond lengths from 2.4451 (6) to 2.4800 (6) Å and bond angles from 105.507 (18) to 117.232 (16) °.

Four cations and two anions pack into inversion related sub-units linked by C–H···Cl and offset π-stacking interactions, Fig. 2. Each of these sub-units is surrounded by six others, Figure 3. Intermolecular π-π stacking interactions between the C4 and C10 pyridyl rings (symmetry operation 1 + x, 1/2 - y, 1/2 + z) are observed along the a axis, with a perpendicular distance between the ring planes of 3.6015 Å. Further π-π stacking interactions between the C8-pyridyl ring and its symmetry partner at (1 - x,1 - y,1 - z) are also observed along the a axis, with a perpendicular distance between the ring planes of 3.6934 Å.

Related literature top

For diagnostic applications of tetrazoles, see: Benon et al. (1980). For related structures, see: Předota et al. (1991) and Morsy et al. (2007).

Experimental top

The title compound was synthesized by a hydrothermal method. A mixture of 2,3,5-triphenyl-2 h-tetrazolium chloride (0.25 g), CdCl2.2.5H2O(0.144 g, 0.50 mmol), and H2O (10 mL) was mechanically stirred at room temperature in air reaching a final pH of 5.0. The solution was then transferred to and sealed in a 37.5 mL Teflon-lined reactor which was heated at 443 K for 4 days. Then the reactor was opened to the air and after cooling to room temperature, colorless block-like crystals were isolated from the resulting mixture.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the inversion related subunits of (I).
[Figure 3] Fig. 3. Packing diagram for (I) viewed down the a axis.
Bis(2,3,5-triphenyltetrazolium) tetrachloridocadmate(II) top
Crystal data top
(C19H15N4)2[CdCl4]F(000) = 1720
Mr = 852.90Dx = 1.511 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 31115 reflections
a = 12.207 (2) Åθ = 3.2–27.5°
b = 15.254 (3) ŵ = 0.91 mm−1
c = 20.132 (4) ÅT = 153 K
β = 90.73 (3)°Block, colorless
V = 3748.4 (13) Å30.24 × 0.22 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		8568 independent reflections
Radiation source: fine-focus sealed tube7790 reflections with I > 2σ(I)
graphiteRint = 0.017
φ and ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.812, Tmax = 0.868k = −19→19
35919 measured reflectionsl = −26→26
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)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0278P)2 + 1.8818P]
where P = (Fo2 + 2Fc2)/3
8568 reflections(Δ/σ)max = 0.001
460 parametersΔρmax = 0.95 e Å−3
0 restraintsΔρmin = −0.45 e Å−3
Crystal data top
(C19H15N4)2[CdCl4]V = 3748.4 (13) Å3
Mr = 852.90Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.207 (2) ŵ = 0.91 mm−1
b = 15.254 (3) ÅT = 153 K
c = 20.132 (4) Å0.24 × 0.22 × 0.16 mm
β = 90.73 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		8568 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		7790 reflections with I > 2σ(I)
Tmin = 0.812, Tmax = 0.868Rint = 0.017
35919 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.022H-atom parameters constrained
wR(F2) = 0.058Δρmax = 0.95 e Å−3
S = 1.09Δρmin = −0.45 e Å−3
8568 reflectionsAbsolute structure: ?
460 parametersFlack parameter: ?
0 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
Cd10.714725 (9)0.234715 (7)0.156523 (5)0.02065 (4)
Cl10.69331 (4)0.07695 (3)0.17345 (2)0.03064 (9)
Cl20.90043 (3)0.28875 (3)0.12929 (2)0.02984 (9)
Cl30.58886 (3)0.28616 (2)0.067656 (17)0.02120 (7)
Cl40.66298 (3)0.30323 (3)0.262572 (17)0.02458 (8)
N10.28772 (10)0.78597 (8)0.06939 (6)0.0181 (2)
N20.46597 (11)0.79913 (8)0.09433 (6)0.0196 (2)
N30.32786 (10)0.70996 (8)0.08724 (6)0.0172 (2)
N41.16473 (11)0.27541 (9)0.03994 (6)0.0211 (3)
N51.16603 (11)0.22688 (8)0.09388 (6)0.0193 (2)
N60.43434 (10)0.71756 (8)0.10180 (6)0.0181 (2)
N71.05604 (11)0.15861 (8)0.02597 (6)0.0204 (3)
N81.10206 (10)0.15691 (8)0.08531 (6)0.0184 (2)
C11.17519 (14)0.04745 (11)0.16212 (8)0.0255 (3)
H1B1.24600.06660.15360.031*
C20.50584 (12)0.64480 (10)0.11877 (8)0.0207 (3)
C31.08506 (13)0.08649 (10)0.13188 (7)0.0194 (3)
C40.97900 (13)0.22698 (11)−0.10237 (8)0.0249 (3)
H4B0.94700.1756−0.08700.030*
C50.37427 (12)0.84022 (9)0.07391 (7)0.0179 (3)
C61.06337 (13)0.26663 (10)−0.06641 (7)0.0214 (3)
C71.09531 (13)0.23275 (10)−0.00113 (7)0.0201 (3)
C80.28952 (15)1.04843 (11)−0.00965 (8)0.0287 (4)
H8A0.23891.0673−0.04150.034*
C91.11354 (16)0.34246 (11)−0.09007 (8)0.0295 (4)
H9A1.17110.3681−0.06640.035*
C100.20113 (15)0.50241 (12)0.14217 (10)0.0332 (4)
H10A0.20090.46490.17860.040*
C110.36276 (15)1.10763 (11)0.01861 (9)0.0299 (4)
H11A0.36131.16610.00550.036*
C120.54656 (14)0.59573 (11)0.06708 (8)0.0284 (3)
H12A0.53100.61020.02310.034*
C131.21644 (15)0.29460 (12)0.26792 (8)0.0291 (4)
H13A1.17950.29880.30790.035*
C140.26513 (12)0.62984 (9)0.08774 (7)0.0192 (3)
C151.32978 (13)0.28155 (11)0.14890 (9)0.0262 (3)
H15A1.36680.27660.10900.031*
C160.29176 (13)0.96112 (10)0.00953 (8)0.0233 (3)
H16A0.24240.9214−0.00910.028*
C170.36847 (12)0.93340 (10)0.05690 (7)0.0188 (3)
C180.13693 (14)0.53840 (12)0.03213 (9)0.0315 (4)
H18A0.09330.5250−0.00470.038*
C190.26649 (14)0.57716 (11)0.14365 (8)0.0262 (3)
H19A0.30930.59110.18070.031*
C200.94289 (15)0.26472 (13)−0.16149 (9)0.0313 (4)
H20A0.88650.2386−0.18590.038*
C210.44200 (13)0.99264 (10)0.08539 (8)0.0232 (3)
H21A0.49320.97380.11690.028*
C220.20176 (13)0.61304 (11)0.03161 (8)0.0233 (3)
H22A0.20270.6503−0.00490.028*
C230.97874 (13)0.05929 (10)0.14174 (8)0.0231 (3)
H23A0.92030.08620.11970.028*
C241.16301 (14)0.26143 (11)0.21197 (8)0.0234 (3)
H24A1.09010.24400.21350.028*
C251.22195 (12)0.25521 (10)0.15412 (7)0.0193 (3)
C260.61160 (16)0.52405 (12)0.08323 (10)0.0365 (4)
H26A0.64060.48950.04970.044*
C270.59140 (17)0.55454 (14)0.19931 (10)0.0410 (5)
H27A0.60670.54010.24330.049*
C280.13662 (15)0.48343 (11)0.08718 (11)0.0357 (4)
H28A0.09270.43360.08700.043*
C291.07672 (18)0.37922 (13)−0.14926 (9)0.0373 (4)
H29A1.10980.4296−0.16560.045*
C300.99065 (17)0.34099 (13)−0.18406 (8)0.0357 (4)
H30A0.96480.3669−0.22300.043*
C311.05005 (16)−0.04896 (11)0.21749 (8)0.0309 (4)
H31A1.0381−0.09450.24720.037*
C320.52652 (15)0.62680 (12)0.18486 (9)0.0322 (4)
H32A0.49810.66170.21840.039*
C330.63346 (16)0.50377 (12)0.14888 (10)0.0379 (4)
H33A0.67690.45550.15930.045*
C341.38103 (14)0.31553 (12)0.20490 (9)0.0324 (4)
H34A1.45330.33450.20280.039*
C350.96171 (15)−0.00952 (11)0.18556 (8)0.0282 (3)
H35A0.8910−0.02920.19350.034*
C360.43818 (14)1.08006 (11)0.06637 (9)0.0290 (4)
H36A0.48621.12020.08570.035*
C371.15587 (15)−0.02118 (11)0.20551 (9)0.0301 (4)
H37A1.2145−0.04880.22670.036*
C381.32453 (15)0.32131 (12)0.26427 (9)0.0320 (4)
H38A1.35980.34340.30190.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.02031 (6)0.02291 (6)0.01869 (6)−0.00040 (4)−0.00164 (4)0.00029 (4)
Cl10.0350 (2)0.02315 (19)0.0337 (2)−0.00084 (16)−0.00361 (17)0.00242 (16)
Cl20.02000 (18)0.0354 (2)0.0341 (2)−0.00039 (15)0.00095 (16)0.00203 (17)
Cl30.02154 (17)0.02392 (17)0.01808 (15)−0.00071 (13)−0.00155 (13)0.00113 (13)
Cl40.02743 (19)0.02940 (19)0.01689 (16)−0.00481 (15)−0.00084 (14)−0.00108 (14)
N10.0201 (6)0.0165 (6)0.0176 (6)0.0021 (5)0.0020 (5)−0.0004 (5)
N20.0218 (6)0.0173 (6)0.0197 (6)0.0004 (5)0.0008 (5)−0.0016 (5)
N30.0163 (6)0.0167 (6)0.0185 (6)0.0012 (5)0.0004 (5)−0.0008 (5)
N40.0227 (6)0.0218 (6)0.0189 (6)0.0014 (5)0.0022 (5)0.0021 (5)
N50.0196 (6)0.0194 (6)0.0188 (6)0.0001 (5)0.0002 (5)0.0005 (5)
N60.0175 (6)0.0164 (6)0.0202 (6)0.0007 (5)−0.0012 (5)−0.0017 (5)
N70.0214 (6)0.0221 (6)0.0178 (6)0.0027 (5)−0.0014 (5)0.0000 (5)
N80.0181 (6)0.0201 (6)0.0172 (5)0.0008 (5)0.0007 (5)0.0002 (5)
C10.0259 (8)0.0231 (8)0.0273 (8)0.0038 (6)−0.0036 (6)−0.0010 (6)
C20.0186 (7)0.0172 (7)0.0263 (7)0.0023 (6)−0.0031 (6)0.0000 (6)
C30.0248 (7)0.0165 (7)0.0169 (6)0.0009 (6)0.0009 (6)0.0007 (5)
C40.0233 (8)0.0300 (8)0.0216 (7)0.0061 (6)0.0029 (6)0.0002 (6)
C50.0193 (7)0.0186 (7)0.0159 (6)0.0012 (5)0.0016 (5)−0.0026 (5)
C60.0244 (8)0.0229 (7)0.0169 (7)0.0063 (6)0.0037 (6)0.0001 (6)
C70.0203 (7)0.0207 (7)0.0194 (7)0.0029 (6)0.0022 (6)−0.0011 (6)
C80.0333 (9)0.0262 (8)0.0268 (8)0.0099 (7)0.0060 (7)0.0045 (7)
C90.0388 (10)0.0265 (8)0.0231 (7)−0.0007 (7)0.0036 (7)0.0011 (6)
C100.0320 (9)0.0222 (8)0.0458 (10)0.0033 (7)0.0089 (8)0.0111 (7)
C110.0354 (9)0.0173 (7)0.0374 (9)0.0050 (7)0.0158 (7)0.0034 (7)
C120.0309 (9)0.0263 (8)0.0278 (8)0.0070 (7)−0.0020 (7)−0.0023 (7)
C130.0369 (9)0.0293 (8)0.0211 (7)−0.0005 (7)−0.0007 (7)−0.0008 (6)
C140.0179 (7)0.0148 (6)0.0250 (7)−0.0001 (5)0.0026 (6)−0.0020 (6)
C150.0195 (7)0.0295 (8)0.0296 (8)0.0011 (6)0.0032 (6)−0.0025 (7)
C160.0250 (8)0.0225 (7)0.0224 (7)0.0028 (6)0.0018 (6)−0.0011 (6)
C170.0197 (7)0.0168 (7)0.0201 (7)0.0019 (5)0.0061 (6)−0.0004 (5)
C180.0237 (8)0.0304 (9)0.0405 (9)−0.0048 (7)0.0015 (7)−0.0114 (7)
C190.0260 (8)0.0235 (8)0.0291 (8)0.0037 (6)0.0005 (7)0.0046 (6)
C200.0292 (9)0.0418 (10)0.0228 (8)0.0128 (7)−0.0022 (7)−0.0038 (7)
C210.0204 (7)0.0208 (7)0.0286 (8)0.0008 (6)0.0045 (6)−0.0030 (6)
C220.0208 (7)0.0250 (8)0.0243 (7)−0.0002 (6)0.0028 (6)−0.0026 (6)
C230.0231 (7)0.0208 (7)0.0255 (7)0.0005 (6)0.0000 (6)0.0003 (6)
C240.0230 (8)0.0250 (8)0.0221 (7)−0.0015 (6)−0.0003 (6)0.0009 (6)
C250.0186 (7)0.0197 (7)0.0196 (7)0.0010 (5)−0.0019 (6)−0.0010 (5)
C260.0379 (10)0.0277 (9)0.0436 (10)0.0125 (8)−0.0036 (8)−0.0102 (8)
C270.0471 (11)0.0392 (11)0.0364 (10)0.0108 (9)−0.0153 (9)0.0054 (8)
C280.0286 (9)0.0189 (8)0.0598 (12)−0.0049 (7)0.0064 (8)−0.0030 (8)
C290.0576 (12)0.0276 (9)0.0269 (8)0.0049 (8)0.0054 (8)0.0071 (7)
C300.0506 (11)0.0370 (10)0.0194 (7)0.0202 (9)0.0027 (7)0.0041 (7)
C310.0490 (11)0.0177 (7)0.0258 (8)−0.0013 (7)−0.0022 (7)0.0014 (6)
C320.0346 (9)0.0346 (9)0.0273 (8)0.0100 (8)−0.0074 (7)−0.0031 (7)
C330.0375 (10)0.0241 (9)0.0517 (11)0.0107 (7)−0.0127 (9)0.0012 (8)
C340.0213 (8)0.0337 (9)0.0421 (10)−0.0011 (7)−0.0068 (7)−0.0041 (8)
C350.0323 (9)0.0209 (8)0.0316 (8)−0.0052 (7)0.0043 (7)0.0008 (7)
C360.0254 (8)0.0195 (8)0.0425 (9)−0.0030 (6)0.0099 (7)−0.0049 (7)
C370.0391 (10)0.0218 (8)0.0292 (8)0.0071 (7)−0.0099 (7)0.0011 (7)
C380.0348 (9)0.0311 (9)0.0298 (8)0.0002 (7)−0.0135 (7)−0.0037 (7)
Geometric parameters (Å, °) top
Cd1—Cl12.4450 (6)C13—C241.390 (2)
Cd1—Cl42.4666 (6)C13—H13A0.9300
Cd1—Cl32.4712 (8)C14—C191.383 (2)
Cd1—Cl22.4801 (6)C14—C221.385 (2)
N1—N31.3073 (18)C15—C251.382 (2)
N1—C51.3442 (19)C15—C341.383 (2)
N2—N61.3120 (18)C15—H15A0.9300
N2—C51.3428 (19)C16—C171.394 (2)
N3—N61.3339 (17)C16—H16A0.9300
N3—C141.4424 (19)C17—C211.392 (2)
N4—N51.3142 (18)C18—C221.387 (2)
N4—C71.344 (2)C18—C281.390 (3)
N5—N81.3323 (18)C18—H18A0.9300
N5—C251.4498 (19)C19—H19A0.9300
N6—C21.4500 (19)C20—C301.381 (3)
N7—N81.3139 (17)C20—H20A0.9300
N7—C71.346 (2)C21—C361.388 (2)
N8—C31.4425 (19)C21—H21A0.9300
C1—C31.385 (2)C22—H22A0.9300
C1—C371.386 (2)C23—C351.388 (2)
C1—H1B0.9300C23—H23A0.9300
C2—C321.379 (2)C24—C251.380 (2)
C2—C121.380 (2)C24—H24A0.9300
C3—C231.379 (2)C26—C331.380 (3)
C4—C201.389 (2)C26—H26A0.9300
C4—C61.390 (2)C27—C331.381 (3)
C4—H4B0.9300C27—C321.386 (3)
C5—C171.464 (2)C27—H27A0.9300
C6—C91.395 (2)C28—H28A0.9300
C6—C71.461 (2)C29—C301.384 (3)
C8—C161.387 (2)C29—H29A0.9300
C8—C111.388 (3)C30—H30A0.9300
C8—H8A0.9300C31—C371.384 (3)
C9—C291.387 (2)C31—C351.386 (3)
C9—H9A0.9300C31—H31A0.9300
C10—C281.381 (3)C32—H32A0.9300
C10—C191.392 (2)C33—H33A0.9300
C10—H10A0.9300C34—C381.390 (3)
C11—C361.388 (3)C34—H34A0.9300
C11—H11A0.9300C35—H35A0.9300
C12—C261.387 (2)C36—H36A0.9300
C12—H12A0.9300C37—H37A0.9300
C13—C381.384 (3)C38—H38A0.9300
Cl1—Cd1—Cl4105.508 (18)C8—C16—H16A120.2
Cl1—Cd1—Cl3110.297 (15)C17—C16—H16A120.2
Cl4—Cd1—Cl3109.17 (2)C21—C17—C16120.60 (14)
Cl1—Cd1—Cl2117.232 (16)C21—C17—C5120.33 (14)
Cl4—Cd1—Cl2107.18 (3)C16—C17—C5119.00 (14)
Cl3—Cd1—Cl2107.22 (2)C22—C18—C28120.58 (17)
N3—N1—C5103.64 (12)C22—C18—H18A119.7
N6—N2—C5103.44 (12)C28—C18—H18A119.7
N1—N3—N6110.12 (12)C14—C19—C10117.25 (16)
N1—N3—C14123.80 (12)C14—C19—H19A121.4
N6—N3—C14126.02 (12)C10—C19—H19A121.4
N5—N4—C7103.67 (13)C30—C20—C4120.04 (18)
N4—N5—N8110.08 (12)C30—C20—H20A120.0
N4—N5—C25121.59 (13)C4—C20—H20A120.0
N8—N5—C25128.02 (12)C36—C21—C17119.39 (15)
N2—N6—N3110.16 (12)C36—C21—H21A120.3
N2—N6—C2125.16 (13)C17—C21—H21A120.3
N3—N6—C2124.55 (12)C14—C22—C18117.29 (16)
N8—N7—C7103.58 (12)C14—C22—H22A121.4
N7—N8—N5110.18 (12)C18—C22—H22A121.4
N7—N8—C3122.84 (12)C3—C23—C35117.88 (15)
N5—N8—C3126.96 (12)C3—C23—H23A121.1
C3—C1—C37117.46 (16)C35—C23—H23A121.1
C3—C1—H1B121.3C25—C24—C13117.69 (15)
C37—C1—H1B121.3C25—C24—H24A121.2
C32—C2—C12123.82 (15)C13—C24—H24A121.2
C32—C2—N6118.82 (14)C24—C25—C15123.48 (15)
C12—C2—N6117.34 (14)C24—C25—N5118.78 (14)
C23—C3—C1123.43 (15)C15—C25—N5117.51 (14)
C23—C3—N8117.45 (13)C33—C26—C12120.27 (17)
C1—C3—N8119.06 (14)C33—C26—H26A119.9
C20—C4—C6119.40 (17)C12—C26—H26A119.9
C20—C4—H4B120.3C33—C27—C32120.56 (17)
C6—C4—H4B120.3C33—C27—H27A119.7
N2—C5—N1112.63 (13)C32—C27—H27A119.7
N2—C5—C17124.24 (13)C10—C28—C18120.36 (16)
N1—C5—C17123.12 (13)C10—C28—H28A119.8
C4—C6—C9120.57 (15)C18—C28—H28A119.8
C4—C6—C7120.14 (15)C30—C29—C9120.02 (18)
C9—C6—C7119.15 (15)C30—C29—H29A120.0
N4—C7—N7112.47 (13)C9—C29—H29A120.0
N4—C7—C6122.75 (14)C20—C30—C29120.62 (16)
N7—C7—C6124.71 (14)C20—C30—H30A119.7
C16—C8—C11120.04 (16)C29—C30—H30A119.7
C16—C8—H8A120.0C37—C31—C35120.57 (16)
C11—C8—H8A120.0C37—C31—H31A119.7
C29—C9—C6119.32 (17)C35—C31—H31A119.7
C29—C9—H9A120.3C2—C32—C27117.26 (17)
C6—C9—H9A120.3C2—C32—H32A121.4
C28—C10—C19120.64 (17)C27—C32—H32A121.4
C28—C10—H10A119.7C26—C33—C27120.60 (17)
C19—C10—H10A119.7C26—C33—H33A119.7
C8—C11—C36120.33 (15)C27—C33—H33A119.7
C8—C11—H11A119.8C15—C34—C38120.02 (16)
C36—C11—H11A119.8C15—C34—H34A120.0
C2—C12—C26117.48 (16)C38—C34—H34A120.0
C2—C12—H12A121.3C31—C35—C23120.08 (16)
C26—C12—H12A121.3C31—C35—H35A120.0
C38—C13—C24120.14 (16)C23—C35—H35A120.0
C38—C13—H13A119.9C11—C36—C21120.12 (16)
C24—C13—H13A119.9C11—C36—H36A119.9
C19—C14—C22123.87 (15)C21—C36—H36A119.9
C19—C14—N3119.81 (14)C31—C37—C1120.55 (16)
C22—C14—N3116.23 (13)C31—C37—H37A119.7
C25—C15—C34117.94 (16)C1—C37—H37A119.7
C25—C15—H15A121.0C13—C38—C34120.71 (16)
C34—C15—H15A121.0C13—C38—H38A119.6
C8—C16—C17119.51 (15)C34—C38—H38A119.6
C5—N1—N3—N6−0.19 (15)N6—N3—C14—C22−130.16 (15)
C5—N1—N3—C14−177.63 (13)C11—C8—C16—C17−0.5 (2)
C7—N4—N5—N81.30 (16)C8—C16—C17—C210.5 (2)
C7—N4—N5—C25−172.82 (13)C8—C16—C17—C5−176.49 (14)
C5—N2—N6—N3−0.66 (15)N2—C5—C17—C21−26.7 (2)
C5—N2—N6—C2175.24 (13)N1—C5—C17—C21154.71 (14)
N1—N3—N6—N20.56 (16)N2—C5—C17—C16150.37 (14)
C14—N3—N6—N2177.93 (13)N1—C5—C17—C16−28.3 (2)
N1—N3—N6—C2−175.37 (13)C22—C14—C19—C101.0 (2)
C14—N3—N6—C22.0 (2)N3—C14—C19—C10177.61 (14)
C7—N7—N8—N50.16 (16)C28—C10—C19—C14−1.1 (3)
C7—N7—N8—C3−178.37 (13)C6—C4—C20—C300.0 (2)
N4—N5—N8—N7−0.96 (16)C16—C17—C21—C360.2 (2)
C25—N5—N8—N7172.67 (13)C5—C17—C21—C36177.18 (14)
N4—N5—N8—C3177.49 (13)C19—C14—C22—C18−0.5 (2)
C25—N5—N8—C3−8.9 (2)N3—C14—C22—C18−177.18 (14)
N2—N6—C2—C3287.7 (2)C28—C18—C22—C140.0 (2)
N3—N6—C2—C32−96.95 (19)C1—C3—C23—C351.6 (2)
N2—N6—C2—C12−94.28 (18)N8—C3—C23—C35178.84 (14)
N3—N6—C2—C1281.1 (2)C38—C13—C24—C251.0 (2)
C37—C1—C3—C23−1.5 (2)C13—C24—C25—C15−1.2 (2)
C37—C1—C3—N8−178.68 (14)C13—C24—C25—N5−175.56 (14)
N7—N8—C3—C23−47.3 (2)C34—C15—C25—C240.3 (3)
N5—N8—C3—C23134.40 (16)C34—C15—C25—N5174.74 (15)
N7—N8—C3—C1130.06 (15)N4—N5—C25—C24122.90 (16)
N5—N8—C3—C1−48.2 (2)N8—N5—C25—C24−50.1 (2)
N6—N2—C5—N10.56 (16)N4—N5—C25—C15−51.8 (2)
N6—N2—C5—C17−178.19 (13)N8—N5—C25—C15135.22 (16)
N3—N1—C5—N2−0.24 (16)C2—C12—C26—C330.1 (3)
N3—N1—C5—C17178.53 (13)C19—C10—C28—C180.7 (3)
C20—C4—C6—C9−1.6 (2)C22—C18—C28—C10−0.1 (3)
C20—C4—C6—C7174.10 (14)C6—C9—C29—C300.3 (3)
N5—N4—C7—N7−1.23 (17)C4—C20—C30—C291.8 (3)
N5—N4—C7—C6176.06 (14)C9—C29—C30—C20−2.0 (3)
N8—N7—C7—N40.68 (17)C12—C2—C32—C27−0.6 (3)
N8—N7—C7—C6−176.56 (14)N6—C2—C32—C27177.31 (17)
C4—C6—C7—N4−170.09 (15)C33—C27—C32—C20.4 (3)
C9—C6—C7—N45.7 (2)C12—C26—C33—C27−0.2 (3)
C4—C6—C7—N76.9 (2)C32—C27—C33—C260.0 (3)
C9—C6—C7—N7−177.36 (15)C25—C15—C34—C380.8 (3)
C4—C6—C9—C291.5 (3)C37—C31—C35—C23−0.9 (3)
C7—C6—C9—C29−174.30 (16)C3—C23—C35—C31−0.4 (2)
C16—C8—C11—C36−0.3 (2)C8—C11—C36—C211.1 (3)
C32—C2—C12—C260.3 (3)C17—C21—C36—C11−1.0 (2)
N6—C2—C12—C26−177.60 (16)C35—C31—C37—C11.0 (3)
N1—N3—C14—C19−129.97 (16)C3—C1—C37—C310.1 (2)
N6—N3—C14—C1953.0 (2)C24—C13—C38—C340.1 (3)
N1—N3—C14—C2246.9 (2)C15—C34—C38—C13−1.0 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···Cl3i0.932.813.6362 (19)148
C37—H37A···Cl4ii0.932.713.5271 (18)146
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···Cl3i0.932.813.6362 (19)148
C37—H37A···Cl4ii0.932.713.5271 (18)146
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, y−1/2, −z+1/2.
Acknowledgements top

The authors thank the International Cooperation Bureau of the Chinese Academy of Sciences (project No. GJHZ0527).

references
References top

Benon, H. J. B., Grace, G. S. & Stanley, B. (1980). J. Phys. Chem. 84, 830–833.

Bruker (1998). SMART. Version 5.628. Bruker AXS Inc., Madison, Wisconsin, USA.

Bruker (1999). SAINT (Version 6.02) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.

Morsy, A. M. A., Franz, A. M. & Alshimai, A. M. (2007). Polyhedron. In the Press, Available online 3 December 2006. Full reference available?

Předota, M., Petříček, V., Žák, Z., Głowiak, T. & Novotný, J. (1991). Acta Cryst. C47, 738–740.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.