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

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

doi:10.1107/S160053680702034X

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

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

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 Cd^II 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 π-stacking interactions. Each of these subunits is surrounded by six others. Intermolecular π–π 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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702034X/sj2289sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680702034X/sj2289Isup2.hkl Contains datablock I

CCDC reference: 650536

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.002 Å
R factor = 0.022
wR factor = 0.058
Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  N3      ..       3.29 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  N6      ..       3.26 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C19 H15 N4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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.

Structure description top

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

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

	Fig. 1. View of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. View of the inversion related subunits of (I).
	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
M_r = 852.90	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 31115 reflections
a = 12.207 (2) Å	θ = 3.2–27.5°
b = 15.254 (3) Å	µ = 0.91 mm⁻¹
c = 20.132 (4) Å	T = 153 K
β = 90.73 (3)°	Block, colorless
V = 3748.4 (13) Å³	0.24 × 0.22 × 0.16 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	8568 independent reflections
Radiation source: fine-focus sealed tube	7790 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.812, T_max = 0.868	k = −19→19
35919 measured reflections	l = −26→26

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0278P)² + 1.8818P] where P = (F_o² + 2F_c²)/3
8568 reflections	(Δ/σ)_max = 0.001
460 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

(C₁₉H₁₅N₄)₂[CdCl₄]	V = 3748.4 (13) Å³
M_r = 852.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.207 (2) Å	µ = 0.91 mm⁻¹
b = 15.254 (3) Å	T = 153 K
c = 20.132 (4) Å	0.24 × 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)
T_min = 0.812, T_max = 0.868	R_int = 0.017
35919 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.09	Δρ_max = 0.95 e Å⁻³
8568 reflections	Δρ_min = −0.45 e Å⁻³
460 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
Cd1	0.714725 (9)	0.234715 (7)	0.156523 (5)	0.02065 (4)
Cl1	0.69331 (4)	0.07695 (3)	0.17345 (2)	0.03064 (9)
Cl2	0.90043 (3)	0.28875 (3)	0.12929 (2)	0.02984 (9)
Cl3	0.58886 (3)	0.28616 (2)	0.067656 (17)	0.02120 (7)
Cl4	0.66298 (3)	0.30323 (3)	0.262572 (17)	0.02458 (8)
N1	0.28772 (10)	0.78597 (8)	0.06939 (6)	0.0181 (2)
N2	0.46597 (11)	0.79913 (8)	0.09433 (6)	0.0196 (2)
N3	0.32786 (10)	0.70996 (8)	0.08724 (6)	0.0172 (2)
N4	1.16473 (11)	0.27541 (9)	0.03994 (6)	0.0211 (3)
N5	1.16603 (11)	0.22688 (8)	0.09388 (6)	0.0193 (2)
N6	0.43434 (10)	0.71756 (8)	0.10180 (6)	0.0181 (2)
N7	1.05604 (11)	0.15861 (8)	0.02597 (6)	0.0204 (3)
N8	1.10206 (10)	0.15691 (8)	0.08531 (6)	0.0184 (2)
C1	1.17519 (14)	0.04745 (11)	0.16212 (8)	0.0255 (3)
H1B	1.2460	0.0666	0.1536	0.031*
C2	0.50584 (12)	0.64480 (10)	0.11877 (8)	0.0207 (3)
C3	1.08506 (13)	0.08649 (10)	0.13188 (7)	0.0194 (3)
C4	0.97900 (13)	0.22698 (11)	−0.10237 (8)	0.0249 (3)
H4B	0.9470	0.1756	−0.0870	0.030*
C5	0.37427 (12)	0.84022 (9)	0.07391 (7)	0.0179 (3)
C6	1.06337 (13)	0.26663 (10)	−0.06641 (7)	0.0214 (3)
C7	1.09531 (13)	0.23275 (10)	−0.00113 (7)	0.0201 (3)
C8	0.28952 (15)	1.04843 (11)	−0.00965 (8)	0.0287 (4)
H8A	0.2389	1.0673	−0.0415	0.034*
C9	1.11354 (16)	0.34246 (11)	−0.09007 (8)	0.0295 (4)
H9A	1.1711	0.3681	−0.0664	0.035*
C10	0.20113 (15)	0.50241 (12)	0.14217 (10)	0.0332 (4)
H10A	0.2009	0.4649	0.1786	0.040*
C11	0.36276 (15)	1.10763 (11)	0.01861 (9)	0.0299 (4)
H11A	0.3613	1.1661	0.0055	0.036*
C12	0.54656 (14)	0.59573 (11)	0.06708 (8)	0.0284 (3)
H12A	0.5310	0.6102	0.0231	0.034*
C13	1.21644 (15)	0.29460 (12)	0.26792 (8)	0.0291 (4)
H13A	1.1795	0.2988	0.3079	0.035*
C14	0.26513 (12)	0.62984 (9)	0.08774 (7)	0.0192 (3)
C15	1.32978 (13)	0.28155 (11)	0.14890 (9)	0.0262 (3)
H15A	1.3668	0.2766	0.1090	0.031*
C16	0.29176 (13)	0.96112 (10)	0.00953 (8)	0.0233 (3)
H16A	0.2424	0.9214	−0.0091	0.028*
C17	0.36847 (12)	0.93340 (10)	0.05690 (7)	0.0188 (3)
C18	0.13693 (14)	0.53840 (12)	0.03213 (9)	0.0315 (4)
H18A	0.0933	0.5250	−0.0047	0.038*
C19	0.26649 (14)	0.57716 (11)	0.14365 (8)	0.0262 (3)
H19A	0.3093	0.5911	0.1807	0.031*
C20	0.94289 (15)	0.26472 (13)	−0.16149 (9)	0.0313 (4)
H20A	0.8865	0.2386	−0.1859	0.038*
C21	0.44200 (13)	0.99264 (10)	0.08539 (8)	0.0232 (3)
H21A	0.4932	0.9738	0.1169	0.028*
C22	0.20176 (13)	0.61304 (11)	0.03161 (8)	0.0233 (3)
H22A	0.2027	0.6503	−0.0049	0.028*
C23	0.97874 (13)	0.05929 (10)	0.14174 (8)	0.0231 (3)
H23A	0.9203	0.0862	0.1197	0.028*
C24	1.16301 (14)	0.26143 (11)	0.21197 (8)	0.0234 (3)
H24A	1.0901	0.2440	0.2135	0.028*
C25	1.22195 (12)	0.25521 (10)	0.15412 (7)	0.0193 (3)
C26	0.61160 (16)	0.52405 (12)	0.08323 (10)	0.0365 (4)
H26A	0.6406	0.4895	0.0497	0.044*
C27	0.59140 (17)	0.55454 (14)	0.19931 (10)	0.0410 (5)
H27A	0.6067	0.5401	0.2433	0.049*
C28	0.13662 (15)	0.48343 (11)	0.08718 (11)	0.0357 (4)
H28A	0.0927	0.4336	0.0870	0.043*
C29	1.07672 (18)	0.37922 (13)	−0.14926 (9)	0.0373 (4)
H29A	1.1098	0.4296	−0.1656	0.045*
C30	0.99065 (17)	0.34099 (13)	−0.18406 (8)	0.0357 (4)
H30A	0.9648	0.3669	−0.2230	0.043*
C31	1.05005 (16)	−0.04896 (11)	0.21749 (8)	0.0309 (4)
H31A	1.0381	−0.0945	0.2472	0.037*
C32	0.52652 (15)	0.62680 (12)	0.18486 (9)	0.0322 (4)
H32A	0.4981	0.6617	0.2184	0.039*
C33	0.63346 (16)	0.50377 (12)	0.14888 (10)	0.0379 (4)
H33A	0.6769	0.4555	0.1593	0.045*
C34	1.38103 (14)	0.31553 (12)	0.20490 (9)	0.0324 (4)
H34A	1.4533	0.3345	0.2028	0.039*
C35	0.96171 (15)	−0.00952 (11)	0.18556 (8)	0.0282 (3)
H35A	0.8910	−0.0292	0.1935	0.034*
C36	0.43818 (14)	1.08006 (11)	0.06637 (9)	0.0290 (4)
H36A	0.4862	1.1202	0.0857	0.035*
C37	1.15587 (15)	−0.02118 (11)	0.20551 (9)	0.0301 (4)
H37A	1.2145	−0.0488	0.2267	0.036*
C38	1.32453 (15)	0.32131 (12)	0.26427 (9)	0.0320 (4)
H38A	1.3598	0.3434	0.3019	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02031 (6)	0.02291 (6)	0.01869 (6)	−0.00040 (4)	−0.00164 (4)	0.00029 (4)
Cl1	0.0350 (2)	0.02315 (19)	0.0337 (2)	−0.00084 (16)	−0.00361 (17)	0.00242 (16)
Cl2	0.02000 (18)	0.0354 (2)	0.0341 (2)	−0.00039 (15)	0.00095 (16)	0.00203 (17)
Cl3	0.02154 (17)	0.02392 (17)	0.01808 (15)	−0.00071 (13)	−0.00155 (13)	0.00113 (13)
Cl4	0.02743 (19)	0.02940 (19)	0.01689 (16)	−0.00481 (15)	−0.00084 (14)	−0.00108 (14)
N1	0.0201 (6)	0.0165 (6)	0.0176 (6)	0.0021 (5)	0.0020 (5)	−0.0004 (5)
N2	0.0218 (6)	0.0173 (6)	0.0197 (6)	0.0004 (5)	0.0008 (5)	−0.0016 (5)
N3	0.0163 (6)	0.0167 (6)	0.0185 (6)	0.0012 (5)	0.0004 (5)	−0.0008 (5)
N4	0.0227 (6)	0.0218 (6)	0.0189 (6)	0.0014 (5)	0.0022 (5)	0.0021 (5)
N5	0.0196 (6)	0.0194 (6)	0.0188 (6)	0.0001 (5)	0.0002 (5)	0.0005 (5)
N6	0.0175 (6)	0.0164 (6)	0.0202 (6)	0.0007 (5)	−0.0012 (5)	−0.0017 (5)
N7	0.0214 (6)	0.0221 (6)	0.0178 (6)	0.0027 (5)	−0.0014 (5)	0.0000 (5)
N8	0.0181 (6)	0.0201 (6)	0.0172 (5)	0.0008 (5)	0.0007 (5)	0.0002 (5)
C1	0.0259 (8)	0.0231 (8)	0.0273 (8)	0.0038 (6)	−0.0036 (6)	−0.0010 (6)
C2	0.0186 (7)	0.0172 (7)	0.0263 (7)	0.0023 (6)	−0.0031 (6)	0.0000 (6)
C3	0.0248 (7)	0.0165 (7)	0.0169 (6)	0.0009 (6)	0.0009 (6)	0.0007 (5)
C4	0.0233 (8)	0.0300 (8)	0.0216 (7)	0.0061 (6)	0.0029 (6)	0.0002 (6)
C5	0.0193 (7)	0.0186 (7)	0.0159 (6)	0.0012 (5)	0.0016 (5)	−0.0026 (5)
C6	0.0244 (8)	0.0229 (7)	0.0169 (7)	0.0063 (6)	0.0037 (6)	0.0001 (6)
C7	0.0203 (7)	0.0207 (7)	0.0194 (7)	0.0029 (6)	0.0022 (6)	−0.0011 (6)
C8	0.0333 (9)	0.0262 (8)	0.0268 (8)	0.0099 (7)	0.0060 (7)	0.0045 (7)
C9	0.0388 (10)	0.0265 (8)	0.0231 (7)	−0.0007 (7)	0.0036 (7)	0.0011 (6)
C10	0.0320 (9)	0.0222 (8)	0.0458 (10)	0.0033 (7)	0.0089 (8)	0.0111 (7)
C11	0.0354 (9)	0.0173 (7)	0.0374 (9)	0.0050 (7)	0.0158 (7)	0.0034 (7)
C12	0.0309 (9)	0.0263 (8)	0.0278 (8)	0.0070 (7)	−0.0020 (7)	−0.0023 (7)
C13	0.0369 (9)	0.0293 (8)	0.0211 (7)	−0.0005 (7)	−0.0007 (7)	−0.0008 (6)
C14	0.0179 (7)	0.0148 (6)	0.0250 (7)	−0.0001 (5)	0.0026 (6)	−0.0020 (6)
C15	0.0195 (7)	0.0295 (8)	0.0296 (8)	0.0011 (6)	0.0032 (6)	−0.0025 (7)
C16	0.0250 (8)	0.0225 (7)	0.0224 (7)	0.0028 (6)	0.0018 (6)	−0.0011 (6)
C17	0.0197 (7)	0.0168 (7)	0.0201 (7)	0.0019 (5)	0.0061 (6)	−0.0004 (5)
C18	0.0237 (8)	0.0304 (9)	0.0405 (9)	−0.0048 (7)	0.0015 (7)	−0.0114 (7)
C19	0.0260 (8)	0.0235 (8)	0.0291 (8)	0.0037 (6)	0.0005 (7)	0.0046 (6)
C20	0.0292 (9)	0.0418 (10)	0.0228 (8)	0.0128 (7)	−0.0022 (7)	−0.0038 (7)
C21	0.0204 (7)	0.0208 (7)	0.0286 (8)	0.0008 (6)	0.0045 (6)	−0.0030 (6)
C22	0.0208 (7)	0.0250 (8)	0.0243 (7)	−0.0002 (6)	0.0028 (6)	−0.0026 (6)
C23	0.0231 (7)	0.0208 (7)	0.0255 (7)	0.0005 (6)	0.0000 (6)	0.0003 (6)
C24	0.0230 (8)	0.0250 (8)	0.0221 (7)	−0.0015 (6)	−0.0003 (6)	0.0009 (6)
C25	0.0186 (7)	0.0197 (7)	0.0196 (7)	0.0010 (5)	−0.0019 (6)	−0.0010 (5)
C26	0.0379 (10)	0.0277 (9)	0.0436 (10)	0.0125 (8)	−0.0036 (8)	−0.0102 (8)
C27	0.0471 (11)	0.0392 (11)	0.0364 (10)	0.0108 (9)	−0.0153 (9)	0.0054 (8)
C28	0.0286 (9)	0.0189 (8)	0.0598 (12)	−0.0049 (7)	0.0064 (8)	−0.0030 (8)
C29	0.0576 (12)	0.0276 (9)	0.0269 (8)	0.0049 (8)	0.0054 (8)	0.0071 (7)
C30	0.0506 (11)	0.0370 (10)	0.0194 (7)	0.0202 (9)	0.0027 (7)	0.0041 (7)
C31	0.0490 (11)	0.0177 (7)	0.0258 (8)	−0.0013 (7)	−0.0022 (7)	0.0014 (6)
C32	0.0346 (9)	0.0346 (9)	0.0273 (8)	0.0100 (8)	−0.0074 (7)	−0.0031 (7)
C33	0.0375 (10)	0.0241 (9)	0.0517 (11)	0.0107 (7)	−0.0127 (9)	0.0012 (8)
C34	0.0213 (8)	0.0337 (9)	0.0421 (10)	−0.0011 (7)	−0.0068 (7)	−0.0041 (8)
C35	0.0323 (9)	0.0209 (8)	0.0316 (8)	−0.0052 (7)	0.0043 (7)	0.0008 (7)
C36	0.0254 (8)	0.0195 (8)	0.0425 (9)	−0.0030 (6)	0.0099 (7)	−0.0049 (7)
C37	0.0391 (10)	0.0218 (8)	0.0292 (8)	0.0071 (7)	−0.0099 (7)	0.0011 (7)
C38	0.0348 (9)	0.0311 (9)	0.0298 (8)	0.0002 (7)	−0.0135 (7)	−0.0037 (7)

Geometric parameters (Å, º) top

Cd1—Cl1	2.4450 (6)	C13—C24	1.390 (2)
Cd1—Cl4	2.4666 (6)	C13—H13A	0.9300
Cd1—Cl3	2.4712 (8)	C14—C19	1.383 (2)
Cd1—Cl2	2.4801 (6)	C14—C22	1.385 (2)
N1—N3	1.3073 (18)	C15—C25	1.382 (2)
N1—C5	1.3442 (19)	C15—C34	1.383 (2)
N2—N6	1.3120 (18)	C15—H15A	0.9300
N2—C5	1.3428 (19)	C16—C17	1.394 (2)
N3—N6	1.3339 (17)	C16—H16A	0.9300
N3—C14	1.4424 (19)	C17—C21	1.392 (2)
N4—N5	1.3142 (18)	C18—C22	1.387 (2)
N4—C7	1.344 (2)	C18—C28	1.390 (3)
N5—N8	1.3323 (18)	C18—H18A	0.9300
N5—C25	1.4498 (19)	C19—H19A	0.9300
N6—C2	1.4500 (19)	C20—C30	1.381 (3)
N7—N8	1.3139 (17)	C20—H20A	0.9300
N7—C7	1.346 (2)	C21—C36	1.388 (2)
N8—C3	1.4425 (19)	C21—H21A	0.9300
C1—C3	1.385 (2)	C22—H22A	0.9300
C1—C37	1.386 (2)	C23—C35	1.388 (2)
C1—H1B	0.9300	C23—H23A	0.9300
C2—C32	1.379 (2)	C24—C25	1.380 (2)
C2—C12	1.380 (2)	C24—H24A	0.9300
C3—C23	1.379 (2)	C26—C33	1.380 (3)
C4—C20	1.389 (2)	C26—H26A	0.9300
C4—C6	1.390 (2)	C27—C33	1.381 (3)
C4—H4B	0.9300	C27—C32	1.386 (3)
C5—C17	1.464 (2)	C27—H27A	0.9300
C6—C9	1.395 (2)	C28—H28A	0.9300
C6—C7	1.461 (2)	C29—C30	1.384 (3)
C8—C16	1.387 (2)	C29—H29A	0.9300
C8—C11	1.388 (3)	C30—H30A	0.9300
C8—H8A	0.9300	C31—C37	1.384 (3)
C9—C29	1.387 (2)	C31—C35	1.386 (3)
C9—H9A	0.9300	C31—H31A	0.9300
C10—C28	1.381 (3)	C32—H32A	0.9300
C10—C19	1.392 (2)	C33—H33A	0.9300
C10—H10A	0.9300	C34—C38	1.390 (3)
C11—C36	1.388 (3)	C34—H34A	0.9300
C11—H11A	0.9300	C35—H35A	0.9300
C12—C26	1.387 (2)	C36—H36A	0.9300
C12—H12A	0.9300	C37—H37A	0.9300
C13—C38	1.384 (3)	C38—H38A	0.9300

Cl1—Cd1—Cl4	105.508 (18)	C8—C16—H16A	120.2
Cl1—Cd1—Cl3	110.297 (15)	C17—C16—H16A	120.2
Cl4—Cd1—Cl3	109.17 (2)	C21—C17—C16	120.60 (14)
Cl1—Cd1—Cl2	117.232 (16)	C21—C17—C5	120.33 (14)
Cl4—Cd1—Cl2	107.18 (3)	C16—C17—C5	119.00 (14)
Cl3—Cd1—Cl2	107.22 (2)	C22—C18—C28	120.58 (17)
N3—N1—C5	103.64 (12)	C22—C18—H18A	119.7
N6—N2—C5	103.44 (12)	C28—C18—H18A	119.7
N1—N3—N6	110.12 (12)	C14—C19—C10	117.25 (16)
N1—N3—C14	123.80 (12)	C14—C19—H19A	121.4
N6—N3—C14	126.02 (12)	C10—C19—H19A	121.4
N5—N4—C7	103.67 (13)	C30—C20—C4	120.04 (18)
N4—N5—N8	110.08 (12)	C30—C20—H20A	120.0
N4—N5—C25	121.59 (13)	C4—C20—H20A	120.0
N8—N5—C25	128.02 (12)	C36—C21—C17	119.39 (15)
N2—N6—N3	110.16 (12)	C36—C21—H21A	120.3
N2—N6—C2	125.16 (13)	C17—C21—H21A	120.3
N3—N6—C2	124.55 (12)	C14—C22—C18	117.29 (16)
N8—N7—C7	103.58 (12)	C14—C22—H22A	121.4
N7—N8—N5	110.18 (12)	C18—C22—H22A	121.4
N7—N8—C3	122.84 (12)	C3—C23—C35	117.88 (15)
N5—N8—C3	126.96 (12)	C3—C23—H23A	121.1
C3—C1—C37	117.46 (16)	C35—C23—H23A	121.1
C3—C1—H1B	121.3	C25—C24—C13	117.69 (15)
C37—C1—H1B	121.3	C25—C24—H24A	121.2
C32—C2—C12	123.82 (15)	C13—C24—H24A	121.2
C32—C2—N6	118.82 (14)	C24—C25—C15	123.48 (15)
C12—C2—N6	117.34 (14)	C24—C25—N5	118.78 (14)
C23—C3—C1	123.43 (15)	C15—C25—N5	117.51 (14)
C23—C3—N8	117.45 (13)	C33—C26—C12	120.27 (17)
C1—C3—N8	119.06 (14)	C33—C26—H26A	119.9
C20—C4—C6	119.40 (17)	C12—C26—H26A	119.9
C20—C4—H4B	120.3	C33—C27—C32	120.56 (17)
C6—C4—H4B	120.3	C33—C27—H27A	119.7
N2—C5—N1	112.63 (13)	C32—C27—H27A	119.7
N2—C5—C17	124.24 (13)	C10—C28—C18	120.36 (16)
N1—C5—C17	123.12 (13)	C10—C28—H28A	119.8
C4—C6—C9	120.57 (15)	C18—C28—H28A	119.8
C4—C6—C7	120.14 (15)	C30—C29—C9	120.02 (18)
C9—C6—C7	119.15 (15)	C30—C29—H29A	120.0
N4—C7—N7	112.47 (13)	C9—C29—H29A	120.0
N4—C7—C6	122.75 (14)	C20—C30—C29	120.62 (16)
N7—C7—C6	124.71 (14)	C20—C30—H30A	119.7
C16—C8—C11	120.04 (16)	C29—C30—H30A	119.7
C16—C8—H8A	120.0	C37—C31—C35	120.57 (16)
C11—C8—H8A	120.0	C37—C31—H31A	119.7
C29—C9—C6	119.32 (17)	C35—C31—H31A	119.7
C29—C9—H9A	120.3	C2—C32—C27	117.26 (17)
C6—C9—H9A	120.3	C2—C32—H32A	121.4
C28—C10—C19	120.64 (17)	C27—C32—H32A	121.4
C28—C10—H10A	119.7	C26—C33—C27	120.60 (17)
C19—C10—H10A	119.7	C26—C33—H33A	119.7
C8—C11—C36	120.33 (15)	C27—C33—H33A	119.7
C8—C11—H11A	119.8	C15—C34—C38	120.02 (16)
C36—C11—H11A	119.8	C15—C34—H34A	120.0
C2—C12—C26	117.48 (16)	C38—C34—H34A	120.0
C2—C12—H12A	121.3	C31—C35—C23	120.08 (16)
C26—C12—H12A	121.3	C31—C35—H35A	120.0
C38—C13—C24	120.14 (16)	C23—C35—H35A	120.0
C38—C13—H13A	119.9	C11—C36—C21	120.12 (16)
C24—C13—H13A	119.9	C11—C36—H36A	119.9
C19—C14—C22	123.87 (15)	C21—C36—H36A	119.9
C19—C14—N3	119.81 (14)	C31—C37—C1	120.55 (16)
C22—C14—N3	116.23 (13)	C31—C37—H37A	119.7
C25—C15—C34	117.94 (16)	C1—C37—H37A	119.7
C25—C15—H15A	121.0	C13—C38—C34	120.71 (16)
C34—C15—H15A	121.0	C13—C38—H38A	119.6
C8—C16—C17	119.51 (15)	C34—C38—H38A	119.6

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—N8	1.30 (16)	C8—C16—C17—C21	0.5 (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—C2	175.24 (13)	N1—C5—C17—C21	154.71 (14)
N1—N3—N6—N2	0.56 (16)	N2—C5—C17—C16	150.37 (14)
C14—N3—N6—N2	177.93 (13)	N1—C5—C17—C16	−28.3 (2)
N1—N3—N6—C2	−175.37 (13)	C22—C14—C19—C10	1.0 (2)
C14—N3—N6—C2	2.0 (2)	N3—C14—C19—C10	177.61 (14)
C7—N7—N8—N5	0.16 (16)	C28—C10—C19—C14	−1.1 (3)
C7—N7—N8—C3	−178.37 (13)	C6—C4—C20—C30	0.0 (2)
N4—N5—N8—N7	−0.96 (16)	C16—C17—C21—C36	0.2 (2)
C25—N5—N8—N7	172.67 (13)	C5—C17—C21—C36	177.18 (14)
N4—N5—N8—C3	177.49 (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—C32	87.7 (2)	C28—C18—C22—C14	0.0 (2)
N3—N6—C2—C32	−96.95 (19)	C1—C3—C23—C35	1.6 (2)
N2—N6—C2—C12	−94.28 (18)	N8—C3—C23—C35	178.84 (14)
N3—N6—C2—C12	81.1 (2)	C38—C13—C24—C25	1.0 (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—C24	0.3 (3)
N5—N8—C3—C23	134.40 (16)	C34—C15—C25—N5	174.74 (15)
N7—N8—C3—C1	130.06 (15)	N4—N5—C25—C24	122.90 (16)
N5—N8—C3—C1	−48.2 (2)	N8—N5—C25—C24	−50.1 (2)
N6—N2—C5—N1	0.56 (16)	N4—N5—C25—C15	−51.8 (2)
N6—N2—C5—C17	−178.19 (13)	N8—N5—C25—C15	135.22 (16)
N3—N1—C5—N2	−0.24 (16)	C2—C12—C26—C33	0.1 (3)
N3—N1—C5—C17	178.53 (13)	C19—C10—C28—C18	0.7 (3)
C20—C4—C6—C9	−1.6 (2)	C22—C18—C28—C10	−0.1 (3)
C20—C4—C6—C7	174.10 (14)	C6—C9—C29—C30	0.3 (3)
N5—N4—C7—N7	−1.23 (17)	C4—C20—C30—C29	1.8 (3)
N5—N4—C7—C6	176.06 (14)	C9—C29—C30—C20	−2.0 (3)
N8—N7—C7—N4	0.68 (17)	C12—C2—C32—C27	−0.6 (3)
N8—N7—C7—C6	−176.56 (14)	N6—C2—C32—C27	177.31 (17)
C4—C6—C7—N4	−170.09 (15)	C33—C27—C32—C2	0.4 (3)
C9—C6—C7—N4	5.7 (2)	C12—C26—C33—C27	−0.2 (3)
C4—C6—C7—N7	6.9 (2)	C32—C27—C33—C26	0.0 (3)
C9—C6—C7—N7	−177.36 (15)	C25—C15—C34—C38	0.8 (3)
C4—C6—C9—C29	1.5 (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—C21	1.1 (3)
C32—C2—C12—C26	0.3 (3)	C17—C21—C36—C11	−1.0 (2)
N6—C2—C12—C26	−177.60 (16)	C35—C31—C37—C1	1.0 (3)
N1—N3—C14—C19	−129.97 (16)	C3—C1—C37—C31	0.1 (2)
N6—N3—C14—C19	53.0 (2)	C24—C13—C38—C34	0.1 (3)
N1—N3—C14—C22	46.9 (2)	C15—C34—C38—C13	−1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cl3ⁱ	0.93	2.81	3.6362 (19)	148
C37—H37A···Cl4ⁱⁱ	0.93	2.71	3.5271 (18)	146

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

Experimental details

Crystal data
Chemical formula	(C₁₉H₁₅N₄)₂[CdCl₄]
M_r	852.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	12.207 (2), 15.254 (3), 20.132 (4)
β (°)	90.73 (3)
V (Å³)	3748.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.24 × 0.22 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.812, 0.868
No. of measured, independent and observed [I > 2σ(I)] reflections	35919, 8568, 7790
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.058, 1.09
No. of reflections	8568
No. of parameters	460
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −0.45

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···Cl3ⁱ	0.93	2.81	3.6362 (19)	148.2
C37—H37A···Cl4ⁱⁱ	0.93	2.71	3.5271 (18)	146.4

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

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