Bis[2-(1H-1,2,4-triazol-1-yl-κN2)-1,10-phenanthroline-κ2N,N′]cadmium(II) bis­(perchlorate)

Li, H.L.

doi:10.1107/S1600536809038768

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1280

https://doi.org/10.1107/S1600536809038768

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Bis[2-(1H-1,2,4-triazol-1-yl-κN²)-1,10-phenanthroline-κ²N,N′]cadmium(II) bis(perchlorate)

Hong Liang Li ^a ^*

^aDepartment of Chemistry, Dezhou University, Dezhou 253023, People's Republic of China
^*Correspondence e-mail: hongliangl1968@yahoo.com.cn

(Received 21 September 2009; accepted 24 September 2009; online 3 October 2009)

In the title complex, [Cd(C₁₄H₉N₅)₂](ClO₄)₂, the Cd^II ion is coordinated by two tridentate 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline ligands in a distorted octahedral CdN₆ environment. In both 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline ligands, the 1,2,4-triazolyl ring and the 1,10-phenanthroline ring system are essentially coplanar [maximun deviations of 0.136 (7) and 0.273 (5) Å, respectively]. The dihedral angle between the mean planes of the ligands is 89.65 (4)°. In the crystal structure, there is a weak π–π stacking interaction between a pyridine ring and a symmetry-related benzene ring with a centroid–centroid distance of 3.772 (3) Å.

Related literature

For related structures, see: Li (2008 ); Liu et al. (2008 ).

Experimental

Crystal data

[Cd(C₁₄H₉N₅)₂](ClO₄)₂
M_r = 805.82
Monoclinic, C 2/c
a = 16.894 (3) Å
b = 26.153 (5) Å
c = 15.574 (3) Å
β = 118.482 (2)°
V = 6048 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 298 K
0.39 × 0.34 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.704, T_max = 0.766
17197 measured reflections
6543 independent reflections
4596 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.162
S = 1.08
6543 reflections
442 parameters
H-atom parameters constrained
Δρ_max = 1.44 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809038768/lh2911sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809038768/lh2911Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry (see e.g. Li, 2008; Liu et al. 2008), but until now the crystal structure of complexes with 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline as a ligand have not been reported. The crystal structure of the title complex is reported herein.

The asymmetric unit of the title complex is shown in Fig. 1. The Cd^II ion is coordinated in a distorted octahedral environment. In both 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline ligands, the 1,2,4-triazolyl ring and the 1,10-phenanthroline ring system are essentially co-planar within 0.0657 Å (for the ligand containing atom N1) and 0.1073 Å (for the ligand containing atom N6) with a maximun deviations of 0.136 (7) Å and 0.273 (5) Å for atom C6 and atom C27, respectively, and the dihedral angle between the two planes is 89.65 (4)°. In the crystal structure, there is a weak π–π stacking interaction involving a symmetry pyridine ring and symmetry related benzene ring, with the relevant distances being Cg1···Cg2ⁱ = 3.772 (3) Å and Cg1···Cg2ⁱ_perp = 3.517 Å [symmetry code: (i) 1 - x, -y, 1 - z; Cg1 and Cg2 are the centroids of C1—C5/N2 ring and C4—C9 ring].

Related literature top

For related structures, see: Li (2008); Liu et al. (2008).

Experimental top

5 ml H₂O solution of hydrated cadmium perchlorate (0.0535 g, 0.128 mmol) was added into 10 ml methanol solution of 2-(1H-1,2,4-triazol-1-yl)-1,10-phenanthroline (0.0631 g, 0.255 mmol) and the mixed soluton was stirred for a few minutes. Yellow single crystals were obtained after the filtrate was allowed to stand at room temperature for two weeks.

Structure description top

For related structures, see: Li (2008); Liu et al. (2008).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme and displacement ellipsoids shown at the 30% probability level

Bis[2-(1H-1,2,4-triazol-1-yl-κN¹)-1,10-phenanthroline- κ²N,N']cadmium(II) bis(perchlorate) top

Crystal data top

[Cd(C₁₄H₉N₅)₂](ClO₄)₂	F(000) = 3216
M_r = 805.82	D_x = 1.770 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6564 reflections
a = 16.894 (3) Å	θ = 2.6–27.7°
b = 26.153 (5) Å	µ = 0.97 mm⁻¹
c = 15.574 (3) Å	T = 298 K
β = 118.482 (2)°	Block, yellow
V = 6048 (2) Å³	0.39 × 0.34 × 0.29 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	6543 independent reflections
Radiation source: fine-focus sealed tube	4596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.704, T_max = 0.766	k = −28→33
17197 measured reflections	l = −19→19

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0899P)² + 4.5706P] where P = (F_o² + 2F_c²)/3
6543 reflections	(Δ/σ)_max = 0.008
442 parameters	Δρ_max = 1.44 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Cd(C₁₄H₉N₅)₂](ClO₄)₂	V = 6048 (2) Å³
M_r = 805.82	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.894 (3) Å	µ = 0.97 mm⁻¹
b = 26.153 (5) Å	T = 298 K
c = 15.574 (3) Å	0.39 × 0.34 × 0.29 mm
β = 118.482 (2)°

Data collection top

Bruker SMART APEX CCD diffractometer	6543 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4596 reflections with I > 2σ(I)
T_min = 0.704, T_max = 0.766	R_int = 0.042
17197 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.08	Δρ_max = 1.44 e Å⁻³
6543 reflections	Δρ_min = −0.47 e Å⁻³
442 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
C1	0.5127 (3)	0.1182 (2)	0.4227 (5)	0.0694 (16)
H1	0.5150	0.1532	0.4338	0.083*
C2	0.5935 (4)	0.0909 (3)	0.4576 (5)	0.0799 (19)
H2	0.6483	0.1079	0.4915	0.096*
C3	0.5919 (3)	0.0404 (2)	0.4420 (5)	0.0727 (17)
H3	0.6456	0.0224	0.4642	0.087*
C4	0.5090 (3)	0.0145 (2)	0.3922 (4)	0.0592 (13)
C5	0.4305 (3)	0.04410 (17)	0.3603 (4)	0.0475 (11)
C6	0.5000 (4)	−0.0394 (2)	0.3739 (5)	0.0759 (18)
H6	0.5516	−0.0588	0.3913	0.091*
C7	0.4194 (4)	−0.0627 (2)	0.3325 (5)	0.0731 (17)
H7	0.4163	−0.0980	0.3247	0.088*
C8	0.3382 (3)	−0.03361 (17)	0.3001 (4)	0.0486 (11)
C9	0.3439 (3)	0.01938 (17)	0.3114 (3)	0.0427 (10)
C10	0.2515 (4)	−0.05463 (18)	0.2560 (4)	0.0586 (13)
H10	0.2449	−0.0899	0.2496	0.070*
C11	0.1767 (3)	−0.02478 (17)	0.2222 (4)	0.0516 (12)
H11	0.1190	−0.0387	0.1916	0.062*
C12	0.1911 (3)	0.02789 (15)	0.2361 (3)	0.0391 (9)
C13	0.0294 (3)	0.05598 (18)	0.1521 (4)	0.0597 (14)
H13	0.0013	0.0243	0.1328	0.072*
C14	0.0545 (4)	0.1336 (2)	0.1739 (5)	0.082 (2)
H14	0.0445	0.1686	0.1719	0.099*
C15	0.3177 (4)	0.1891 (2)	0.1320 (4)	0.0642 (14)
H15	0.2954	0.1584	0.0992	0.077*
C16	0.3438 (4)	0.2265 (3)	0.0876 (5)	0.0733 (16)
H16	0.3413	0.2202	0.0276	0.088*
C17	0.3730 (4)	0.2721 (2)	0.1323 (5)	0.0706 (16)
H17	0.3902	0.2974	0.1026	0.085*
C18	0.3535 (3)	0.24079 (16)	0.2655 (4)	0.0453 (11)
C19	0.3776 (3)	0.28132 (19)	0.2236 (4)	0.0580 (14)
C20	0.4052 (3)	0.3288 (2)	0.2756 (5)	0.0639 (15)
H20	0.4212	0.3558	0.2480	0.077*
C21	0.4088 (3)	0.33548 (18)	0.3603 (5)	0.0650 (16)
H21	0.4277	0.3669	0.3916	0.078*
C22	0.3583 (3)	0.24799 (16)	0.3577 (4)	0.0453 (11)
C23	0.3839 (3)	0.29504 (16)	0.4074 (4)	0.0508 (12)
C24	0.3833 (3)	0.29919 (18)	0.4969 (4)	0.0565 (14)
H24	0.3966	0.3304	0.5293	0.068*
C25	0.3637 (3)	0.25823 (19)	0.5368 (4)	0.0537 (12)
H25	0.3648	0.2604	0.5969	0.064*
C26	0.3419 (3)	0.21271 (17)	0.4836 (3)	0.0449 (11)
C27	0.3297 (4)	0.1559 (2)	0.6069 (4)	0.0661 (14)
H27	0.3577	0.1766	0.6619	0.079*
C28	0.2613 (3)	0.0968 (2)	0.5116 (4)	0.0598 (13)
H28	0.2302	0.0663	0.4879	0.072*
Cd1	0.28772 (2)	0.135509 (12)	0.30429 (3)	0.04704 (15)
Cl1	0.13943 (10)	0.06057 (5)	0.95941 (12)	0.0702 (4)
Cl2	0.10794 (8)	0.28026 (5)	0.15282 (10)	0.0570 (3)
N1	0.2704 (2)	0.04897 (13)	0.2791 (3)	0.0386 (8)
N2	0.4328 (3)	0.09551 (14)	0.3743 (3)	0.0531 (10)
N3	0.1183 (2)	0.06236 (13)	0.2033 (3)	0.0453 (9)
N4	0.1360 (3)	0.11365 (14)	0.2175 (3)	0.0534 (10)
N5	−0.0133 (3)	0.09957 (18)	0.1326 (5)	0.0868 (18)
N6	0.2755 (3)	0.12904 (14)	0.4555 (3)	0.0503 (9)
N7	0.2948 (4)	0.1110 (2)	0.6053 (4)	0.0757 (14)
N8	0.3199 (2)	0.16812 (15)	0.5189 (3)	0.0462 (9)
N9	0.3383 (2)	0.20762 (13)	0.3991 (3)	0.0412 (8)
N10	0.3231 (3)	0.19511 (15)	0.2187 (3)	0.0501 (9)
O1	0.1678 (5)	0.0166 (2)	0.9378 (7)	0.176 (3)
O2	0.2009 (8)	0.0683 (6)	1.0566 (7)	0.278 (7)
O3	0.1713 (6)	0.1011 (3)	0.9279 (7)	0.178 (3)
O4	0.0568 (4)	0.0603 (3)	0.9342 (11)	0.310 (9)
O5	0.0794 (4)	0.2506 (2)	0.0682 (4)	0.1056 (17)
O6	0.0358 (3)	0.30873 (18)	0.1493 (4)	0.1030 (17)
O7	0.1776 (3)	0.31420 (17)	0.1655 (4)	0.1020 (18)
O8	0.1407 (4)	0.24674 (18)	0.2350 (3)	0.0993 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.042 (3)	0.059 (3)	0.094 (4)	−0.008 (2)	0.021 (3)	0.006 (3)
C2	0.038 (3)	0.087 (5)	0.097 (5)	−0.011 (3)	0.018 (3)	0.015 (4)
C3	0.038 (3)	0.078 (4)	0.096 (5)	0.008 (3)	0.028 (3)	0.010 (3)
C4	0.046 (3)	0.062 (3)	0.073 (4)	0.014 (2)	0.031 (3)	0.008 (3)
C5	0.040 (2)	0.047 (3)	0.055 (3)	0.0001 (19)	0.021 (2)	−0.001 (2)
C6	0.051 (3)	0.063 (4)	0.107 (5)	0.020 (3)	0.032 (3)	−0.006 (3)
C7	0.062 (3)	0.048 (3)	0.092 (4)	0.015 (3)	0.023 (3)	−0.009 (3)
C8	0.054 (3)	0.039 (2)	0.052 (3)	0.004 (2)	0.026 (2)	−0.005 (2)
C9	0.041 (2)	0.043 (2)	0.047 (2)	0.0028 (18)	0.023 (2)	−0.0007 (19)
C10	0.063 (3)	0.033 (2)	0.074 (4)	−0.003 (2)	0.028 (3)	−0.011 (2)
C11	0.045 (2)	0.037 (2)	0.068 (3)	−0.0058 (19)	0.023 (2)	−0.009 (2)
C12	0.039 (2)	0.037 (2)	0.039 (2)	−0.0017 (17)	0.0164 (19)	−0.0045 (17)
C13	0.037 (2)	0.039 (2)	0.082 (4)	−0.0066 (19)	0.011 (2)	−0.001 (2)
C14	0.043 (3)	0.043 (3)	0.115 (5)	0.005 (2)	0.001 (3)	0.000 (3)
C15	0.064 (3)	0.064 (3)	0.071 (4)	−0.002 (3)	0.038 (3)	−0.001 (3)
C16	0.069 (4)	0.094 (5)	0.068 (4)	0.007 (3)	0.041 (3)	0.012 (3)
C17	0.056 (3)	0.081 (4)	0.081 (4)	0.005 (3)	0.037 (3)	0.031 (3)
C18	0.0301 (19)	0.038 (2)	0.061 (3)	0.0026 (17)	0.017 (2)	0.005 (2)
C19	0.037 (2)	0.050 (3)	0.084 (4)	0.006 (2)	0.026 (3)	0.021 (3)
C20	0.042 (3)	0.047 (3)	0.094 (4)	0.000 (2)	0.026 (3)	0.020 (3)
C21	0.046 (3)	0.033 (2)	0.094 (4)	−0.006 (2)	0.015 (3)	0.002 (3)
C22	0.0260 (19)	0.035 (2)	0.063 (3)	0.0003 (16)	0.012 (2)	0.002 (2)
C23	0.029 (2)	0.034 (2)	0.072 (3)	0.0014 (17)	0.009 (2)	0.002 (2)
C24	0.039 (2)	0.043 (3)	0.065 (3)	0.0014 (19)	0.007 (2)	−0.020 (2)
C25	0.035 (2)	0.054 (3)	0.056 (3)	0.004 (2)	0.009 (2)	−0.013 (2)
C26	0.0277 (19)	0.047 (2)	0.052 (3)	0.0050 (17)	0.0134 (19)	−0.005 (2)
C27	0.072 (4)	0.067 (3)	0.053 (3)	0.002 (3)	0.024 (3)	−0.001 (3)
C28	0.053 (3)	0.053 (3)	0.074 (4)	0.006 (2)	0.030 (3)	0.007 (3)
Cd1	0.0425 (2)	0.0334 (2)	0.0606 (3)	−0.00736 (12)	0.02088 (17)	−0.00628 (14)
Cl1	0.0631 (8)	0.0591 (8)	0.0876 (11)	−0.0039 (6)	0.0353 (8)	0.0056 (7)
Cl2	0.0429 (6)	0.0549 (7)	0.0676 (8)	−0.0099 (5)	0.0218 (6)	−0.0054 (6)
N1	0.0362 (17)	0.0336 (17)	0.0435 (19)	0.0004 (14)	0.0170 (16)	−0.0021 (15)
N2	0.040 (2)	0.045 (2)	0.070 (3)	−0.0043 (16)	0.023 (2)	0.0012 (19)
N3	0.0385 (18)	0.0323 (18)	0.055 (2)	−0.0049 (14)	0.0139 (17)	−0.0016 (16)
N4	0.042 (2)	0.0306 (18)	0.073 (3)	−0.0002 (16)	0.015 (2)	−0.0007 (18)
N5	0.037 (2)	0.054 (3)	0.124 (4)	−0.001 (2)	0.002 (3)	0.001 (3)
N6	0.045 (2)	0.046 (2)	0.056 (2)	−0.0054 (16)	0.0210 (19)	−0.0009 (18)
N7	0.092 (4)	0.078 (3)	0.069 (3)	0.004 (3)	0.048 (3)	0.011 (3)
N8	0.0382 (19)	0.052 (2)	0.046 (2)	0.0004 (16)	0.0179 (17)	−0.0018 (18)
N9	0.0326 (17)	0.0335 (18)	0.053 (2)	0.0004 (14)	0.0171 (16)	−0.0003 (16)
N10	0.047 (2)	0.049 (2)	0.056 (2)	0.0022 (17)	0.0256 (19)	0.0061 (18)
O1	0.150 (6)	0.085 (4)	0.294 (10)	0.035 (4)	0.106 (6)	0.011 (5)
O2	0.228 (11)	0.47 (2)	0.156 (8)	−0.129 (12)	0.111 (8)	−0.059 (10)
O3	0.188 (7)	0.104 (5)	0.223 (8)	−0.025 (5)	0.083 (6)	0.050 (5)
O4	0.064 (4)	0.128 (6)	0.64 (2)	−0.014 (4)	0.089 (8)	−0.112 (9)
O5	0.125 (4)	0.123 (4)	0.086 (3)	−0.046 (3)	0.065 (3)	−0.039 (3)
O6	0.053 (2)	0.088 (3)	0.156 (5)	−0.001 (2)	0.040 (3)	−0.016 (3)
O7	0.052 (2)	0.072 (3)	0.172 (5)	−0.018 (2)	0.045 (3)	−0.001 (3)
O8	0.126 (4)	0.080 (3)	0.085 (3)	−0.011 (3)	0.045 (3)	0.005 (2)

Geometric parameters (Å, º) top

C1—N2	1.331 (6)	C18—C19	1.403 (6)
C1—C2	1.399 (8)	C18—C22	1.412 (7)
C1—H1	0.9300	C19—C20	1.434 (8)
C2—C3	1.343 (8)	C20—C21	1.304 (9)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.409 (7)	C21—C23	1.458 (7)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.406 (6)	C22—N9	1.362 (6)
C4—C6	1.430 (8)	C22—C23	1.407 (6)
C5—N2	1.359 (6)	C23—C24	1.403 (8)
C5—C9	1.440 (6)	C24—C25	1.356 (7)
C6—C7	1.343 (8)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.396 (6)
C7—C8	1.435 (7)	C25—H25	0.9300
C7—H7	0.9300	C26—N9	1.294 (6)
C8—C9	1.395 (6)	C26—N8	1.413 (6)
C8—C10	1.400 (7)	C27—N7	1.310 (8)
C9—N1	1.340 (5)	C27—N8	1.338 (7)
C10—C11	1.359 (7)	C27—H27	0.9300
C10—H10	0.9300	C28—N6	1.316 (6)
C11—C12	1.398 (6)	C28—N7	1.341 (7)
C11—H11	0.9300	C28—H28	0.9300
C12—N1	1.300 (5)	Cd1—N1	2.292 (3)
C12—N3	1.410 (5)	Cd1—N9	2.295 (3)
C13—N5	1.305 (6)	Cd1—N10	2.307 (4)
C13—N3	1.333 (6)	Cd1—N4	2.327 (4)
C13—H13	0.9300	Cd1—N2	2.396 (4)
C14—N4	1.318 (7)	Cd1—N6	2.465 (4)
C14—N5	1.347 (7)	Cl1—O4	1.257 (7)
C14—H14	0.9300	Cl1—O1	1.349 (7)
C15—N10	1.319 (7)	Cl1—O3	1.380 (7)
C15—C16	1.385 (8)	Cl1—O2	1.382 (10)
C15—H15	0.9300	Cl2—O5	1.402 (5)
C16—C17	1.350 (8)	Cl2—O6	1.407 (5)
C16—H16	0.9300	Cl2—O7	1.410 (4)
C17—C19	1.408 (9)	Cl2—O8	1.428 (5)
C17—H17	0.9300	N3—N4	1.369 (5)
C18—N10	1.366 (6)	N6—N8	1.370 (5)

N2—C1—C2	122.1 (5)	C25—C24—C23	120.9 (4)
N2—C1—H1	119.0	C25—C24—H24	119.6
C2—C1—H1	119.0	C23—C24—H24	119.6
C3—C2—C1	120.0 (5)	C24—C25—C26	117.1 (5)
C3—C2—H2	120.0	C24—C25—H25	121.5
C1—C2—H2	120.0	C26—C25—H25	121.5
C2—C3—C4	120.1 (5)	N9—C26—C25	124.2 (5)
C2—C3—H3	119.9	N9—C26—N8	114.7 (4)
C4—C3—H3	119.9	C25—C26—N8	121.1 (5)
C5—C4—C3	116.9 (5)	N7—C27—N8	111.1 (5)
C5—C4—C6	118.7 (5)	N7—C27—H27	124.5
C3—C4—C6	124.4 (5)	N8—C27—H27	124.5
N2—C5—C4	122.5 (4)	N6—C28—N7	115.5 (5)
N2—C5—C9	118.3 (4)	N6—C28—H28	122.3
C4—C5—C9	119.2 (4)	N7—C28—H28	122.3
C7—C6—C4	122.0 (5)	N1—Cd1—N9	154.12 (13)
C7—C6—H6	119.0	N1—Cd1—N10	127.99 (14)
C4—C6—H6	119.0	N9—Cd1—N10	72.38 (14)
C6—C7—C8	120.6 (5)	N1—Cd1—N4	69.07 (12)
C6—C7—H7	119.7	N9—Cd1—N4	122.99 (13)
C8—C7—H7	119.7	N10—Cd1—N4	110.32 (14)
C9—C8—C10	116.4 (4)	N1—Cd1—N2	70.49 (12)
C9—C8—C7	119.1 (4)	N9—Cd1—N2	94.59 (13)
C10—C8—C7	124.5 (4)	N10—Cd1—N2	93.84 (14)
N1—C9—C8	122.0 (4)	N4—Cd1—N2	139.56 (13)
N1—C9—C5	117.7 (4)	N1—Cd1—N6	91.92 (12)
C8—C9—C5	120.3 (4)	N9—Cd1—N6	67.45 (13)
C11—C10—C8	121.7 (4)	N10—Cd1—N6	139.53 (14)
C11—C10—H10	119.1	N4—Cd1—N6	88.13 (15)
C8—C10—H10	119.1	N2—Cd1—N6	93.95 (14)
C10—C11—C12	116.4 (4)	O4—Cl1—O1	113.0 (5)
C10—C11—H11	121.8	O4—Cl1—O3	117.2 (7)
C12—C11—H11	121.8	O1—Cl1—O3	108.7 (6)
N1—C12—C11	124.0 (4)	O4—Cl1—O2	119.1 (9)
N1—C12—N3	115.0 (3)	O1—Cl1—O2	103.1 (8)
C11—C12—N3	121.1 (4)	O3—Cl1—O2	93.4 (6)
N5—C13—N3	111.7 (4)	O5—Cl2—O6	110.7 (4)
N5—C13—H13	124.1	O5—Cl2—O7	111.7 (3)
N3—C13—H13	124.1	O6—Cl2—O7	108.8 (3)
N4—C14—N5	115.3 (5)	O5—Cl2—O8	108.4 (3)
N4—C14—H14	122.4	O6—Cl2—O8	108.5 (4)
N5—C14—H14	122.4	O7—Cl2—O8	108.7 (3)
N10—C15—C16	123.0 (6)	C12—N1—C9	119.4 (4)
N10—C15—H15	118.5	C12—N1—Cd1	121.5 (3)
C16—C15—H15	118.5	C9—N1—Cd1	119.1 (3)
C17—C16—C15	119.4 (6)	C1—N2—C5	118.4 (4)
C17—C16—H16	120.3	C1—N2—Cd1	127.2 (4)
C15—C16—H16	120.3	C5—N2—Cd1	114.4 (3)
C16—C17—C19	120.2 (5)	C13—N3—N4	108.4 (3)
C16—C17—H17	119.9	C13—N3—C12	132.6 (4)
C19—C17—H17	119.9	N4—N3—C12	118.8 (3)
N10—C18—C19	122.1 (5)	C14—N4—N3	102.1 (4)
N10—C18—C22	118.9 (4)	C14—N4—Cd1	142.4 (3)
C19—C18—C22	118.9 (4)	N3—N4—Cd1	115.4 (3)
C18—C19—C17	116.8 (5)	C13—N5—C14	102.4 (4)
C18—C19—C20	118.7 (5)	C28—N6—N8	102.1 (4)
C17—C19—C20	124.5 (5)	C28—N6—Cd1	143.4 (4)
C21—C20—C19	122.2 (5)	N8—N6—Cd1	111.8 (3)
C21—C20—H20	118.9	C27—N7—C28	102.8 (5)
C19—C20—H20	118.9	C27—N8—N6	108.6 (4)
C20—C21—C23	121.8 (5)	C27—N8—C26	131.9 (4)
C20—C21—H21	119.1	N6—N8—C26	119.4 (4)
C23—C21—H21	119.1	C26—N9—C22	120.0 (4)
N9—C22—C23	119.9 (5)	C26—N9—Cd1	124.1 (3)
N9—C22—C18	118.2 (4)	C22—N9—Cd1	115.6 (3)
C23—C22—C18	121.9 (4)	C15—N10—C18	118.4 (4)
C24—C23—C22	117.9 (4)	C15—N10—Cd1	126.9 (4)
C24—C23—C21	125.7 (5)	C18—N10—Cd1	114.7 (3)
C22—C23—C21	116.4 (5)

N2—C1—C2—C3	0.3 (11)	N4—Cd1—N2—C5	1.2 (5)
C1—C2—C3—C4	−1.2 (11)	N6—Cd1—N2—C5	92.9 (4)
C2—C3—C4—C5	0.3 (9)	N5—C13—N3—N4	−0.9 (7)
C2—C3—C4—C6	−178.5 (7)	N5—C13—N3—C12	−175.9 (5)
C3—C4—C5—N2	1.4 (8)	N1—C12—N3—C13	175.5 (5)
C6—C4—C5—N2	−179.7 (6)	C11—C12—N3—C13	−4.6 (8)
C3—C4—C5—C9	−178.3 (5)	N1—C12—N3—N4	0.9 (6)
C6—C4—C5—C9	0.6 (8)	C11—C12—N3—N4	−179.2 (5)
C5—C4—C6—C7	−3.9 (10)	N5—C14—N4—N3	−0.6 (8)
C3—C4—C6—C7	174.9 (7)	N5—C14—N4—Cd1	179.9 (5)
C4—C6—C7—C8	3.3 (11)	C13—N3—N4—C14	0.8 (6)
C6—C7—C8—C9	0.6 (9)	C12—N3—N4—C14	176.6 (5)
C6—C7—C8—C10	179.8 (6)	C13—N3—N4—Cd1	−179.4 (4)
C10—C8—C9—N1	−2.0 (7)	C12—N3—N4—Cd1	−3.6 (5)
C7—C8—C9—N1	177.2 (5)	N1—Cd1—N4—C14	−177.1 (8)
C10—C8—C9—C5	176.9 (5)	N9—Cd1—N4—C14	28.8 (8)
C7—C8—C9—C5	−3.8 (8)	N10—Cd1—N4—C14	−52.9 (8)
N2—C5—C9—N1	2.4 (7)	N2—Cd1—N4—C14	−175.9 (7)
C4—C5—C9—N1	−177.8 (4)	N6—Cd1—N4—C14	90.2 (8)
N2—C5—C9—C8	−176.5 (5)	N1—Cd1—N4—N3	3.4 (3)
C4—C5—C9—C8	3.2 (7)	N9—Cd1—N4—N3	−150.8 (3)
C9—C8—C10—C11	2.7 (8)	N10—Cd1—N4—N3	127.5 (3)
C7—C8—C10—C11	−176.5 (6)	N2—Cd1—N4—N3	4.5 (5)
C8—C10—C11—C12	−1.5 (8)	N6—Cd1—N4—N3	−89.4 (3)
C10—C11—C12—N1	−0.5 (8)	N3—C13—N5—C14	0.5 (8)
C10—C11—C12—N3	179.5 (5)	N4—C14—N5—C13	0.1 (10)
N10—C15—C16—C17	−2.7 (9)	N7—C28—N6—N8	−1.9 (6)
C15—C16—C17—C19	0.6 (9)	N7—C28—N6—Cd1	155.8 (4)
N10—C18—C19—C17	−2.9 (7)	N1—Cd1—N6—C28	−3.2 (6)
C22—C18—C19—C17	179.1 (4)	N9—Cd1—N6—C28	−167.1 (6)
N10—C18—C19—C20	177.4 (4)	N10—Cd1—N6—C28	−174.4 (5)
C22—C18—C19—C20	−0.7 (6)	N4—Cd1—N6—C28	65.8 (6)
C16—C17—C19—C18	2.0 (7)	N2—Cd1—N6—C28	−73.7 (6)
C16—C17—C19—C20	−178.2 (5)	N1—Cd1—N6—N8	153.3 (3)
C18—C19—C20—C21	0.1 (7)	N9—Cd1—N6—N8	−10.6 (3)
C17—C19—C20—C21	−179.7 (5)	N10—Cd1—N6—N8	−17.9 (4)
C19—C20—C21—C23	−0.6 (8)	N4—Cd1—N6—N8	−137.7 (3)
N10—C18—C22—N9	4.5 (6)	N2—Cd1—N6—N8	82.7 (3)
C19—C18—C22—N9	−177.3 (4)	N8—C27—N7—C28	−1.4 (7)
N10—C18—C22—C23	−176.2 (4)	N6—C28—N7—C27	2.1 (7)
C19—C18—C22—C23	1.9 (6)	N7—C27—N8—N6	0.3 (6)
N9—C22—C23—C24	−3.2 (6)	N7—C27—N8—C26	176.4 (5)
C18—C22—C23—C24	177.5 (4)	C28—N6—N8—C27	1.0 (5)
N9—C22—C23—C21	176.9 (4)	Cd1—N6—N8—C27	−165.0 (3)
C18—C22—C23—C21	−2.3 (6)	C28—N6—N8—C26	−175.7 (4)
C20—C21—C23—C24	−178.2 (5)	Cd1—N6—N8—C26	18.4 (4)
C20—C21—C23—C22	1.7 (7)	N9—C26—N8—C27	167.5 (5)
C22—C23—C24—C25	3.8 (6)	C25—C26—N8—C27	−13.6 (7)
C21—C23—C24—C25	−176.4 (4)	N9—C26—N8—N6	−16.7 (5)
C23—C24—C25—C26	−1.8 (6)	C25—C26—N8—N6	162.1 (4)
C24—C25—C26—N9	−0.8 (6)	C25—C26—N9—C22	1.3 (6)
C24—C25—C26—N8	−179.6 (4)	N8—C26—N9—C22	−179.8 (3)
C11—C12—N1—C9	1.2 (7)	C25—C26—N9—Cd1	−173.1 (3)
N3—C12—N1—C9	−178.9 (4)	N8—C26—N9—Cd1	5.7 (5)
C11—C12—N1—Cd1	−177.4 (4)	C23—C22—N9—C26	0.8 (6)
N3—C12—N1—Cd1	2.5 (5)	C18—C22—N9—C26	−180.0 (4)
C8—C9—N1—C12	0.2 (7)	C23—C22—N9—Cd1	175.7 (3)
C5—C9—N1—C12	−178.8 (4)	C18—C22—N9—Cd1	−5.1 (5)
C8—C9—N1—Cd1	178.8 (4)	N1—Cd1—N9—C26	−36.7 (5)
C5—C9—N1—Cd1	−0.2 (5)	N10—Cd1—N9—C26	177.7 (3)
N9—Cd1—N1—C12	119.9 (4)	N4—Cd1—N9—C26	74.5 (4)
N10—Cd1—N1—C12	−103.2 (3)	N2—Cd1—N9—C26	−89.7 (3)
N4—Cd1—N1—C12	−3.3 (3)	N6—Cd1—N9—C26	2.7 (3)
N2—Cd1—N1—C12	177.5 (4)	N1—Cd1—N9—C22	148.6 (3)
N6—Cd1—N1—C12	84.0 (3)	N10—Cd1—N9—C22	3.0 (3)
N9—Cd1—N1—C9	−58.7 (5)	N4—Cd1—N9—C22	−100.2 (3)
N10—Cd1—N1—C9	78.2 (4)	N2—Cd1—N9—C22	95.6 (3)
N4—Cd1—N1—C9	178.1 (4)	N6—Cd1—N9—C22	−172.0 (3)
N2—Cd1—N1—C9	−1.1 (3)	C16—C15—N10—C18	1.9 (8)
N6—Cd1—N1—C9	−94.6 (3)	C16—C15—N10—Cd1	−177.4 (4)
C2—C1—N2—C5	1.3 (9)	C19—C18—N10—C15	1.0 (6)
C2—C1—N2—Cd1	−177.7 (5)	C22—C18—N10—C15	179.0 (4)
C4—C5—N2—C1	−2.2 (8)	C19—C18—N10—Cd1	−179.7 (3)
C9—C5—N2—C1	177.5 (5)	C22—C18—N10—Cd1	−1.6 (5)
C4—C5—N2—Cd1	177.0 (4)	N1—Cd1—N10—C15	16.8 (5)
C9—C5—N2—Cd1	−3.3 (6)	N9—Cd1—N10—C15	178.6 (4)
N1—Cd1—N2—C1	−178.6 (5)	N4—Cd1—N10—C15	−62.0 (4)
N9—Cd1—N2—C1	−20.3 (5)	N2—Cd1—N10—C15	85.0 (4)
N10—Cd1—N2—C1	52.3 (5)	N6—Cd1—N10—C15	−174.4 (4)
N4—Cd1—N2—C1	−179.7 (5)	N1—Cd1—N10—C18	−162.5 (3)
N6—Cd1—N2—C1	−87.9 (5)	N9—Cd1—N10—C18	−0.7 (3)
N1—Cd1—N2—C5	2.3 (3)	N4—Cd1—N10—C18	118.7 (3)
N9—Cd1—N2—C5	160.6 (4)	N2—Cd1—N10—C18	−94.3 (3)
N10—Cd1—N2—C5	−126.8 (4)	N6—Cd1—N10—C18	6.3 (4)

Experimental details

Crystal data
Chemical formula	[Cd(C₁₄H₉N₅)₂](ClO₄)₂
M_r	805.82
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	16.894 (3), 26.153 (5), 15.574 (3)
β (°)	118.482 (2)
V (Å³)	6048 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.97
Crystal size (mm)	0.39 × 0.34 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.704, 0.766
No. of measured, independent and observed [I > 2σ(I)] reflections	17197, 6543, 4596
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.162, 1.08
No. of reflections	6543
No. of parameters	442
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.44, −0.47

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, J. M. (2008). Acta Cryst. E64, m982. Web of Science CrossRef IUCr Journals Google Scholar
Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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