[2-Amino-4,6-bis-(2-pyrid-yl)-1,3,5-tri-azine-κN,N,N]dichloridocadmium(II).

In the title compound, [CdCl(2)(C(13)H(10)N(6))], 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, mol-ecules are linked via N-H⋯N, N-H⋯Cl and C-H⋯Cl hydrogen bonds into a supra-molecular 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 = 433.58

Triclinic,

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[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.056

S = 1.01

2588 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CdCl2(C13H10N6)]	Z = 2
Mr = 433.58	F(000) = 424
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0354P)2 + 0.2818P] where P = (Fo2 + 2Fc2)/3
2588 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cl1iv	0.97	2.75	3.705 (3)	166
C11—H11A···Cl2v	0.97	2.82	3.596 (2)	138

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⋯Cl1iv	0.97	2.75	3.705 (3)	166
C11—H11A⋯Cl2v	0.97	2.82	3.596 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .