[2-Amino-4,6-bis­(2-pyrid­yl)-1,3,5-tri­azine-κ3N4,N5,N6]dichloridocadmium(II)

Cao, M.-L.; Shi, L.

doi:10.1107/S1600536811012517

metal-organic compounds

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Volume 67| Part 5| May 2011| Page m638

doi:10.1107/S1600536811012517

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[2-Amino-4,6-bis(2-pyridyl)-1,3,5-triazine-κ³N⁴,N⁵,N⁶]dichloridocadmium(II)

Man-Li Cao ^a ^* and Lei Shi ^a

^aDepartment of Chemistry, Guangdong University of Education, Guangzhou 510303, People's Republic of China
^*Correspondence e-mail: caoml@mail3.sysu.edu.cn

(Received 8 March 2011; accepted 4 April 2011; online 29 April 2011)

In the title compound, [CdCl₂(C₁₃H₁₀N₆)], the 2-amino-4,6-bis(pyridin-2-yl)-1,3,5-triazine (HABPT) ligand adopts a tridentate tripyridyl coordination mode. The Cd^II atom is five-coordinated by three N atoms from the HABPT ligand and two chloride ions. In the crystal, molecules are linked via N—H⋯N, N—H⋯Cl and C—H⋯Cl hydrogen bonds into a supramolecular network.

Related literature

For asymmetric ligands containing a triazine ring, see: Drew et al. (2000 ); Boubals et al. (2002 ); Medlycott et al. (2007 ); Chi et al. (2006 ); Cao et al. (2008 , 2009 ). For the synthesis of the HABPT ligand, see: Case & Koft (1959 ). For metal complexes of the HABPT ligand, see: Drew et al. (2000); Boubals et al. (2002); Cao et al. (2009). For the diverse coordination modes of rigid multidentate polypyridyl ligands containing a triazine ring as a bridge, see: Zhou, Li, Wu & Zhang (2006 ); Zhou, Li, Zheng, Zhang & Wu (2006 ).

Experimental

Crystal data

[CdCl₂(C₁₃H₁₀N₆)]
M_r = 433.58
Triclinic, $[P \overline 1]$
a = 8.8750 (6) Å
b = 9.2010 (7) Å
c = 10.2677 (7) Å
α = 82.5151 (9)°
β = 65.636 (1)°
γ = 82.798 (1)°
V = 754.89 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.80 mm⁻¹
T = 293 K
0.34 × 0.31 × 0.28 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.581, T_max = 0.636
5102 measured reflections
2588 independent reflections
2499 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.056
S = 1.01
2588 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯N3ⁱ	0.91	2.31	3.183 (3)	162
N6—H6B⋯Cl2ⁱⁱ	0.91	2.45	3.334 (2)	165
C12—H12A⋯Cl1ⁱⁱⁱ	0.97	2.76	3.671 (2)	158
C2—H2A⋯Cl1^iv	0.97	2.75	3.705 (3)	166
C11—H11A⋯Cl2^v	0.97	2.82	3.596 (2)	138
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x, -y+1, -z+1; (iii) -x, -y, -z+2; (iv) -x+1, -y+1, -z+2; (v) x-1, y, z.

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012517/zq2094sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012517/zq2094Isup2.hkl

checkCIF report

Comment top

The rigid multidentate polypyridyl ligands containing a triazine ring as a bridge have attracted greatly our attention due to their coordination diversity (Zhou, Li, Wu & Zhang, 2006); Zhou, Li, Zheng, Zhang & Wu, 2006). Although coordination chemistry of the symmetrical ligands like tri(2-pyridyl)-l,3,5-triazine (TPT) has been well explored, the observations on the asymmetric ligands containing triazine ring are still rare (Drew et al., 2000; Boubals et al., 2002; Medlycott et al., 2007; Chi et al., 2006; Cao et al., 2008, 2009).

The ligand 2-amino-4,6-bis(2-pyridyl)-l,3,5-triazine (HABPT) has five potential coordinate sites, it may offer a tridentate chelating mode or bis-bidentate binding mode with the capability of bridging two metal ions in chelating way (Drew et al. 2000; Boubals et al., 2002; Cao et al., 2009). As a contribution to the synthesis and structural studies of coordination abilities of the ligand (Case et al., 1959; Drew et al., 2000; Boubals et al., 2002 and Cao et al., 2009), we present here the crystal structure of the title compound, a new cadmium(II) complex with the HABPT ligand.

Within the title compound, C₁₃H₁₀CdCl₂N₆, the Cd^II center is five-coordinated respectively by three N atoms [Cd—N1 2.387 (2), Cd—N2 2.2679 (18), Cd—N5 2.433 (2) Å] from the HABPT ligand and two Cl atoms [Cd—Cl1 2.4176 (7) and Cd—Cl2 2.4431 (7) Å]. The ligand adopts a tridentate tripyridyl mode to coordinate to the Cd^II ion. Two chloride ligands are posited up and down the plane of the ligand that further accept hydrogen bonds from other ligands, the deviations values of Cd, Cl1 and Cl2 from the least-squares plane (rms deviation 0.122 Å for all non-H atoms of the planar tridentate ligand) are -0.603 (1), 0.540 (2) and -2.997 (1) Å, respectively. Viewed from the whole crystal structure, molecules are linked by intermolecular N—H···N, N—H···Cl and C—H···Cl hydrogen bonds to form a supramolecular structure. A weak intermolecular π–π interaction between the triazine ring and one pyridyl ring is also observed with a centroid-centroid distance of 3.976 (1) Å.

Related literature top

For asymmetric ligands containing a triazine ring, see: Drew et al. (2000); Boubals et al. (2002); Medlycott et al. (2007); Chi et al. (2006); Cao et al. (2008, 2009). For the synthesis of the HABPT ligand, see: Case & Koft (1959). For metal complexes of the HABPT ligand, see: Drew et al. (2000); Boubals et al. (2002); Cao et al. (2009). For the diverse coordination modes of rigid multidentate polypyridyl ligands containing a triazine ring as a bridge, see: Zhou, Li, Wu & Zhang (2006); Zhou, Li, Zheng, Zhang & Wu (2006).

Experimental top

The ligand HABPT was prepared according to previously reported procedures (F.H. Case et al., 1959). To a suspension of HABPT (0.025 g, 0.1 mmol) in 7 ml of ethanol was added the solution of CdCl₂ (0.018 g, 0.1 mmol) in 7 ml distilled water. The resulting mixture was vibrated under ultrasonic condition for 20 min and then filtered. The obtained colorless filtrate was allowed to stay at ambient temperature for one week giving 0.026 g (60% yield, based on the ligand) of colourless crystals suitable for a structural determination.

Anal. Calcd. for C₁₃H₁₀Cl₂N₆Cd (%): C 36.01, H 2.31, N 19.38; found (%): C 36.12, H 2.40, N 19.31.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

[2-Amino-4,6-bis(2-pyridyl)-1,3,5-triazine- κ³N⁴,N⁵,N⁶]dichloridocadmium(II) top

Crystal data top

[CdCl₂(C₁₃H₁₀N₆)]	Z = 2
M_r = 433.58	F(000) = 424
Triclinic, P1	D_x = 1.908 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8750 (6) Å	Cell parameters from 2588 reflections
b = 9.2010 (7) Å	θ = 2.2–25.0°
c = 10.2677 (7) Å	µ = 1.80 mm⁻¹
α = 82.5151 (9)°	T = 293 K
β = 65.636 (1)°	Block, colourless
γ = 82.798 (1)°	0.34 × 0.31 × 0.28 mm
V = 754.89 (9) Å³

Data collection top

Bruker SMART APEX CCD detector diffractometer	2588 independent reflections
Radiation source: fine-focus sealed tube	2499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.581, T_max = 0.636	k = −10→10
5102 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.056	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0354P)² + 0.2818P] where P = (F_o² + 2F_c²)/3
2588 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[CdCl₂(C₁₃H₁₀N₆)]	γ = 82.798 (1)°
M_r = 433.58	V = 754.89 (9) Å³
Triclinic, P1	Z = 2
a = 8.8750 (6) Å	Mo Kα radiation
b = 9.2010 (7) Å	µ = 1.80 mm⁻¹
c = 10.2677 (7) Å	T = 293 K
α = 82.5151 (9)°	0.34 × 0.31 × 0.28 mm
β = 65.636 (1)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	2588 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2499 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.636	R_int = 0.014
5102 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
2588 reflections	Δρ_min = −0.30 e Å⁻³
199 parameters

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

	x	y	z	U_iso*/U_eq
Cd	0.21372 (2)	0.386656 (17)	0.788019 (17)	0.03420 (8)
Cl1	0.22830 (10)	0.26193 (9)	1.00530 (7)	0.05660 (19)
Cl2	0.41551 (8)	0.26525 (8)	0.58040 (7)	0.04683 (16)
N1	0.2999 (2)	0.6218 (2)	0.7893 (2)	0.0354 (4)
N2	0.0652 (2)	0.5692 (2)	0.7109 (2)	0.0316 (4)
N3	0.0354 (2)	0.8157 (2)	0.6236 (2)	0.0307 (4)
N4	−0.1444 (2)	0.6385 (2)	0.6264 (2)	0.0332 (4)
N5	−0.0378 (2)	0.2992 (2)	0.7962 (2)	0.0352 (4)
N6	−0.1636 (3)	0.8735 (2)	0.5305 (2)	0.0404 (5)
H6A	−0.1322	0.9668	0.5070	0.048*
H6B	−0.2468	0.8494	0.5095	0.048*
C1	0.4108 (3)	0.6446 (3)	0.8398 (3)	0.0444 (6)
H1A	0.4555	0.5567	0.8820	0.053*
C2	0.4571 (3)	0.7822 (3)	0.8394 (3)	0.0472 (6)
H2A	0.5370	0.7896	0.8800	0.057*
C3	0.3859 (3)	0.9019 (3)	0.7847 (3)	0.0467 (6)
H3A	0.4194	0.9989	0.7835	0.056*
C4	0.2714 (3)	0.8806 (3)	0.7307 (3)	0.0377 (5)
H4A	0.2264	0.9664	0.6864	0.045*
C5	0.2318 (3)	0.7398 (3)	0.7343 (2)	0.0303 (5)
C6	0.1044 (3)	0.7081 (2)	0.6848 (2)	0.0290 (5)
C7	−0.0883 (3)	0.7746 (3)	0.5937 (2)	0.0321 (5)
C8	−0.0629 (3)	0.5416 (2)	0.6838 (2)	0.0303 (5)
C9	−0.1177 (3)	0.3903 (2)	0.7273 (2)	0.0311 (5)
C10	−0.2455 (3)	0.3474 (3)	0.7005 (3)	0.0381 (5)
H10A	−0.3033	0.4136	0.6498	0.046*
C11	−0.2923 (3)	0.2053 (3)	0.7456 (3)	0.0481 (6)
H11A	−0.3814	0.1696	0.7309	0.058*
C12	−0.2127 (3)	0.1126 (3)	0.8178 (3)	0.0478 (6)
H12A	−0.2415	0.0132	0.8551	0.057*
C13	−0.0864 (3)	0.1634 (3)	0.8405 (3)	0.0427 (6)
H13A	−0.0270	0.0998	0.8914	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.03892 (12)	0.02984 (12)	0.03786 (12)	0.00290 (8)	−0.02185 (9)	−0.00009 (8)
Cl1	0.0672 (4)	0.0623 (5)	0.0399 (3)	0.0064 (4)	−0.0279 (3)	0.0077 (3)
Cl2	0.0430 (3)	0.0568 (4)	0.0433 (3)	0.0013 (3)	−0.0188 (3)	−0.0137 (3)
N1	0.0387 (10)	0.0315 (11)	0.0427 (11)	0.0007 (8)	−0.0245 (9)	−0.0014 (8)
N2	0.0321 (10)	0.0272 (10)	0.0403 (10)	−0.0013 (8)	−0.0199 (8)	−0.0015 (8)
N3	0.0352 (10)	0.0268 (10)	0.0355 (10)	−0.0027 (8)	−0.0204 (8)	0.0005 (8)
N4	0.0390 (10)	0.0284 (10)	0.0389 (10)	−0.0042 (8)	−0.0236 (9)	0.0023 (8)
N5	0.0368 (10)	0.0294 (11)	0.0401 (11)	−0.0015 (8)	−0.0180 (9)	0.0021 (8)
N6	0.0485 (12)	0.0314 (11)	0.0551 (13)	−0.0068 (9)	−0.0372 (11)	0.0088 (9)
C1	0.0432 (14)	0.0467 (16)	0.0534 (16)	0.0046 (12)	−0.0312 (13)	−0.0062 (12)
C2	0.0435 (14)	0.0562 (18)	0.0551 (16)	−0.0070 (12)	−0.0313 (13)	−0.0081 (13)
C3	0.0494 (15)	0.0447 (16)	0.0565 (16)	−0.0134 (12)	−0.0295 (13)	−0.0030 (12)
C4	0.0429 (13)	0.0329 (13)	0.0436 (13)	−0.0066 (10)	−0.0237 (11)	0.0003 (10)
C5	0.0294 (11)	0.0331 (13)	0.0303 (11)	−0.0029 (9)	−0.0141 (9)	−0.0025 (9)
C6	0.0315 (11)	0.0275 (12)	0.0300 (11)	−0.0012 (9)	−0.0147 (9)	−0.0026 (9)
C7	0.0358 (12)	0.0307 (12)	0.0325 (11)	−0.0027 (9)	−0.0172 (10)	−0.0001 (9)
C8	0.0328 (11)	0.0278 (12)	0.0317 (11)	−0.0017 (9)	−0.0149 (9)	−0.0017 (9)
C9	0.0323 (11)	0.0279 (12)	0.0333 (11)	−0.0016 (9)	−0.0136 (9)	−0.0024 (9)
C10	0.0375 (12)	0.0340 (13)	0.0467 (14)	−0.0033 (10)	−0.0211 (11)	−0.0027 (10)
C11	0.0459 (15)	0.0414 (15)	0.0608 (17)	−0.0142 (12)	−0.0233 (13)	−0.0007 (13)
C12	0.0489 (15)	0.0310 (14)	0.0585 (17)	−0.0117 (11)	−0.0168 (13)	0.0048 (12)
C13	0.0440 (14)	0.0315 (13)	0.0474 (14)	−0.0008 (11)	−0.0166 (12)	0.0065 (11)

Geometric parameters (Å, º) top

Cd—N2	2.2679 (18)	C1—C2	1.378 (4)
Cd—N1	2.387 (2)	C1—H1A	0.9845
Cd—Cl1	2.4176 (7)	C2—C3	1.373 (4)
Cd—N5	2.433 (2)	C2—H2A	0.9723
Cd—Cl2	2.4431 (7)	C3—C4	1.386 (3)
N1—C1	1.336 (3)	C3—H3A	0.9727
N1—C5	1.349 (3)	C4—C5	1.376 (3)
N2—C6	1.331 (3)	C4—H4A	0.9838
N2—C8	1.337 (3)	C5—C6	1.489 (3)
N3—C6	1.324 (3)	C8—C9	1.485 (3)
N3—C7	1.362 (3)	C9—C10	1.384 (3)
N4—C8	1.311 (3)	C10—C11	1.385 (4)
N4—C7	1.356 (3)	C10—H10A	0.9818
N5—C13	1.333 (3)	C11—C12	1.375 (4)
N5—C9	1.348 (3)	C11—H11A	0.9664
N6—C7	1.321 (3)	C12—C13	1.381 (4)
N6—H6A	0.9078	C12—H12A	0.9670
N6—H6B	0.9080	C13—H13A	0.9815

N2—Cd—N1	68.97 (6)	C4—C3—H3A	122.2
N2—Cd—Cl1	141.58 (5)	C5—C4—C3	118.9 (2)
N1—Cd—Cl1	100.97 (5)	C5—C4—H4A	122.6
N2—Cd—N5	69.07 (7)	C3—C4—H4A	118.4
N1—Cd—N5	134.84 (7)	N1—C5—C4	122.3 (2)
Cl1—Cd—N5	101.44 (5)	N1—C5—C6	115.38 (19)
N2—Cd—Cl2	108.57 (5)	C4—C5—C6	122.3 (2)
N1—Cd—Cl2	109.67 (5)	N3—C6—N2	124.7 (2)
Cl1—Cd—Cl2	109.69 (3)	N3—C6—C5	120.0 (2)
N5—Cd—Cl2	98.80 (5)	N2—C6—C5	115.24 (19)
C1—N1—C5	117.9 (2)	N6—C7—N4	116.1 (2)
C1—N1—Cd	124.73 (17)	N6—C7—N3	118.9 (2)
C5—N1—Cd	117.40 (14)	N4—C7—N3	124.9 (2)
C6—N2—C8	116.34 (19)	N4—C8—N2	124.9 (2)
C6—N2—Cd	122.13 (14)	N4—C8—C9	118.8 (2)
C8—N2—Cd	121.48 (15)	N2—C8—C9	116.28 (19)
C6—N3—C7	114.17 (19)	N5—C9—C10	122.5 (2)
C8—N4—C7	114.62 (19)	N5—C9—C8	116.0 (2)
C13—N5—C9	117.9 (2)	C10—C9—C8	121.5 (2)
C13—N5—Cd	125.93 (16)	C9—C10—C11	118.7 (2)
C9—N5—Cd	115.21 (15)	C9—C10—H10A	122.5
C7—N6—H6A	120.1	C11—C10—H10A	118.8
C7—N6—H6B	120.9	C12—C11—C10	119.0 (2)
H6A—N6—H6B	119.0	C12—C11—H11A	118.6
N1—C1—C2	123.1 (2)	C10—C11—H11A	122.4
N1—C1—H1A	115.9	C11—C12—C13	118.9 (2)
C2—C1—H1A	121.0	C11—C12—H12A	123.4
C3—C2—C1	118.6 (2)	C13—C12—H12A	117.7
C3—C2—H2A	123.3	N5—C13—C12	123.0 (2)
C1—C2—H2A	118.0	N5—C13—H13A	116.2
C2—C3—C4	119.2 (2)	C12—C13—H13A	120.8
C2—C3—H3A	118.6

N2—Cd—N1—C1	174.8 (2)	C7—N3—C6—N2	2.9 (3)
Cl1—Cd—N1—C1	33.5 (2)	C7—N3—C6—C5	−175.0 (2)
N5—Cd—N1—C1	152.02 (19)	C8—N2—C6—N3	−6.0 (3)
Cl2—Cd—N1—C1	−82.2 (2)	Cd—N2—C6—N3	171.45 (17)
N2—Cd—N1—C5	−5.55 (16)	C8—N2—C6—C5	172.00 (19)
Cl1—Cd—N1—C5	−146.86 (16)	Cd—N2—C6—C5	−10.6 (3)
N5—Cd—N1—C5	−28.3 (2)	N1—C5—C6—N3	−177.2 (2)
Cl2—Cd—N1—C5	97.44 (16)	C4—C5—C6—N3	5.9 (3)
N1—Cd—N2—C6	8.74 (16)	N1—C5—C6—N2	4.8 (3)
Cl1—Cd—N2—C6	89.73 (18)	C4—C5—C6—N2	−172.2 (2)
N5—Cd—N2—C6	171.65 (19)	C8—N4—C7—N6	177.5 (2)
Cl2—Cd—N2—C6	−95.81 (17)	C8—N4—C7—N3	−3.8 (3)
N1—Cd—N2—C8	−173.96 (19)	C6—N3—C7—N6	−179.0 (2)
Cl1—Cd—N2—C8	−92.97 (18)	C6—N3—C7—N4	2.3 (3)
N5—Cd—N2—C8	−11.05 (17)	C7—N4—C8—N2	0.3 (3)
Cl2—Cd—N2—C8	81.49 (17)	C7—N4—C8—C9	178.3 (2)
N2—Cd—N5—C13	−179.5 (2)	C6—N2—C8—N4	4.2 (3)
N1—Cd—N5—C13	−156.69 (19)	Cd—N2—C8—N4	−173.20 (17)
Cl1—Cd—N5—C13	−38.3 (2)	C6—N2—C8—C9	−173.76 (19)
Cl2—Cd—N5—C13	73.9 (2)	Cd—N2—C8—C9	8.8 (3)
N2—Cd—N5—C9	12.20 (16)	C13—N5—C9—C10	−0.6 (4)
N1—Cd—N5—C9	35.0 (2)	Cd—N5—C9—C10	168.70 (18)
Cl1—Cd—N5—C9	153.32 (16)	C13—N5—C9—C8	178.2 (2)
Cl2—Cd—N5—C9	−94.40 (16)	Cd—N5—C9—C8	−12.4 (3)
C5—N1—C1—C2	0.6 (4)	N4—C8—C9—N5	−174.8 (2)
Cd—N1—C1—C2	−179.7 (2)	N2—C8—C9—N5	3.3 (3)
N1—C1—C2—C3	0.1 (4)	N4—C8—C9—C10	4.0 (3)
C1—C2—C3—C4	−0.6 (4)	N2—C8—C9—C10	−177.8 (2)
C2—C3—C4—C5	0.4 (4)	N5—C9—C10—C11	−0.3 (4)
C1—N1—C5—C4	−0.9 (3)	C8—C9—C10—C11	−179.1 (2)
Cd—N1—C5—C4	179.46 (18)	C9—C10—C11—C12	1.2 (4)
C1—N1—C5—C6	−177.8 (2)	C10—C11—C12—C13	−1.2 (4)
Cd—N1—C5—C6	2.5 (3)	C9—N5—C13—C12	0.6 (4)
C3—C4—C5—N1	0.3 (4)	Cd—N5—C13—C12	−167.4 (2)
C3—C4—C5—C6	177.1 (2)	C11—C12—C13—N5	0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N3ⁱ	0.91	2.31	3.183 (3)	162
N6—H6B···Cl2ⁱⁱ	0.91	2.45	3.334 (2)	165
C12—H12A···Cl1ⁱⁱⁱ	0.97	2.76	3.671 (2)	158
C2—H2A···Cl1^iv	0.97	2.75	3.705 (3)	166
C11—H11A···Cl2^v	0.97	2.82	3.596 (2)	138

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y, −z+2; (iv) −x+1, −y+1, −z+2; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[CdCl₂(C₁₃H₁₀N₆)]
M_r	433.58
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8750 (6), 9.2010 (7), 10.2677 (7)
α, β, γ (°)	82.5151 (9), 65.636 (1), 82.798 (1)
V (Å³)	754.89 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.80
Crystal size (mm)	0.34 × 0.31 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.581, 0.636
No. of measured, independent and observed [I > 2σ(I)] reflections	5102, 2588, 2499
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.056, 1.01
No. of reflections	2588
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N3ⁱ	0.91	2.31	3.183 (3)	162
N6—H6B···Cl2ⁱⁱ	0.91	2.45	3.334 (2)	165
C12—H12A···Cl1ⁱⁱⁱ	0.97	2.76	3.671 (2)	158
C2—H2A···Cl1^iv	0.97	2.75	3.705 (3)	166
C11—H11A···Cl2^v	0.97	2.82	3.596 (2)	138

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x, −y+1, −z+1; (iii) −x, −y, −z+2; (iv) −x+1, −y+1, −z+2; (v) x−1, y, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21001031) and the special research fund for PhDs of Guangdong University of Education (10ARF05).

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