μ-2,3,5,6-Tetra-2-pyridylpyrazine-κ3N1,N2,N6:κ3N3,N4,N5-bis­[(methanol-κO)(nitrato-κ2O,O′)(nitrato-κO)cadmium(II)]

Seyed Sadjadi, M.; Ebadi, A.; Zare, K.; Amani, V.; Khavasi, H.R.

doi:10.1107/S1600536808022320

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1050-m1051

doi:10.1107/S1600536808022320

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μ-2,3,5,6-Tetra-2-pyridylpyrazine-κ³N¹,N²,N⁶:κ³N³,N⁴,N⁵-bis[(methanol-κO)(nitrato-κ²O,O′)(nitrato-κO)cadmium(II)]

Mirabdullah Seyed Sadjadi,^a ^* Amin Ebadi,^a Karim Zare,^b Vahid Amani ^c and Hamid Reza Khavasi ^b

^aDepartment of Chemistry, Science and Research Campus, Islamic Azad University, Poonak, Tehran, Iran, ^bDepartment of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran, and ^cDepartment of Chemistry, Islamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
^*Correspondence e-mail: mirabdullahsadjadi@yahoo.com

(Received 13 July 2008; accepted 16 July 2008; online 19 July 2008)

The title complex, [Cd₂(NO₃)₄(C₂₄H₁₆N₆)(CH₄O)₂], displays a centrosymmetric dinuclear structure, in which the 2,3,5,6-tetra-2-pyridinylpyrazine (tppz) ligand links two Cd ions separated by 7.323 (4) Å. Each Cd^II center is seven-coordinated by three N-atom donors of tppz in one plane, by two O atoms nearly normal to this plane, and by two O atoms 0.393 (3) and 0.488 (3) Å from that plane. The two Cd^II ions are above and below the plane of the pyrazine ring of the tppz ligand, oriented with respect to the pyridine rings at dihedral angles of 38.01 (3) and 31.90 (3)°. The dihedral angle between the two pyridine rings is 41.11 (3)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules.

Related literature

For related literature, see: Bock et al. (1992 ); Carranza et al. (2004 ); Goodwin & Lyons (1959 ); Graf et al. (1993 , 1997 ); Greaves & Stoeckli-Evans (1992 ); Hadadzadeh et al. (2006 ); Laine et al. (1995 ); Sakai & Kurashima (2003 ); Yamada et al. (2000 ); Zhang et al. (2005 ).

Experimental

Crystal data

[Cd₂(NO₃)₄(C₂₄H₁₆N₆)(CH₄O)₂]
M_r = 925.37
Monoclinic, P 2₁ /c
a = 9.0777 (12) Å
b = 10.8949 (9) Å
c = 16.690 (2) Å
β = 93.847 (10)°
V = 1646.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 298 (2) K
0.50 × 0.40 × 0.25 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.510, T_max = 0.710
4664 measured reflections
4642 independent reflections
4223 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.171
S = 1.07
4642 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.00 e Å⁻³
Δρ_min = −0.95 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

O1—Cd1	2.330 (4)
O2—Cd1	2.431 (4)
O3—Cd1	2.476 (4)
O5—Cd1	2.305 (4)
N1—Cd1	2.407 (4)
N2—Cd1	2.359 (4)
N3—Cd1	2.393 (4)

O5—Cd1—O1	150.47 (16)
O5—Cd1—N2	119.29 (16)
O1—Cd1—N2	88.94 (13)
O5—Cd1—N3	94.10 (16)
O1—Cd1—N3	87.79 (13)
N2—Cd1—N3	69.31 (13)
O5—Cd1—N1	106.73 (17)
O1—Cd1—N1	90.37 (14)
N2—Cd1—N1	69.73 (12)
N3—Cd1—N1	139.02 (13)
O5—Cd1—O2	77.34 (15)
O1—Cd1—O2	81.82 (14)
N2—Cd1—O2	149.55 (11)
N3—Cd1—O2	138.56 (14)
N1—Cd1—O2	81.32 (12)
O5—Cd1—O3	72.18 (16)
O1—Cd1—O3	78.57 (14)
N2—Cd1—O3	152.93 (12)
N3—Cd1—O3	86.13 (13)
N1—Cd1—O3	133.44 (13)
O2—Cd1—O3	52.52 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O3ⁱ	0.92 (5)	1.87 (5)	2.788 (5)	172
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022320/hk2497sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022320/hk2497Isup2.hkl

checkCIF report

Comment top

Goodwin & Lyons (1959) were reported the synthesis of 2,3,5,6-tetra- (2-pyridinyl)pyrazine (tppz). Bock et al. (1992) and Greaves & Stoeckli-Evans (1992) were determined the structure of tppz by single crystal X-ray analysis. Among many reported compounds containing tppz, most are complexes of transition metal ions, including ruthenium (Hadadzadeh et al., 2006), platinum (Sakai & Kurashima, 2003), mercury (Zhang et al., 2005), copper (Carranza et al., 2004), iron (Laine et al., 1995), nickel (Graf et al., 1997), palladium (Yamada et al., 2000) and zinc (Graf et al., 1993). For further investigation of 2,3,5,6-tetra(2-pyridinyl)pyrazine, we synthesized the title complex, and report herein its crystal structure.

The title complex is a centrosymmetric dinuclear complex, in which the tppz ligand link two Cd ions separated by 7.323 (4) Å (Fig. 1). Each Cd^II center is seven-coordinated by three N donors of tppz in one plane, two O atoms (O1 and O5) nearly normal to this plane (Table 1) and two O atoms -0.393 (3) Å (for O2) and -0.488 (3) Å (for O3) away from that plane. The two Cd^II ions are above and below the plane of the pyrazine ring B (N2/C6/C7/N2a/C6a/C7a) [symmetry code: (a) 1 - x, -y, -z] of the tppz ligand. The dihedral angles between rings A (N1/C1-C5), B and C (N3/C8-C12) are A/B = 38.01 (3)°, A/C = 41.11 (3)° and B/C = 31.90 (3)°.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 2) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Bock et al. (1992); Carranza et al. (2004); Goodwin & Lyons (1959); Graf et al. (1993, 1997); Greaves & Stoeckli-Evans (1992); Hadadzadeh et al. (2006); Laine et al. (1995); Sakai & Kurashima (2003); Yamada et al. (2000); Zhang et al. (2005).

Experimental top

For the preparation of the title compound, a solution of 2,3,5,6-tetra- (2-pyridinyl)pyrazine (0.4 g, 1 mmol) in HCl₃ (30 ml) was added to a solution of Cd(NO₃)₂.4H₂O (0.62 g, 2 mmol) in methanol (200 ml) and the resulting colorless solution was stirred for 15 min at room temperature. Then, it was left to evaporate slowly at room temperature. After one week, colorless prismatic crystals of the title compound were isolated (yield; 0.71 g, 76.73%, m.p < 573 k).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level [symmetry code: (a) 1 - x, -y, -z].
	Fig. 2. A packing diagram for the title molecule. Hydrogen bonds are shown as dashed lines.

µ-2,3,5,6-Tetra-2-pyridylpyrazine- κ³N¹,N²,N⁶:κ³N³,N⁴,N⁵- bis[(methanol-κO)(nitrato-κ²O,O')(nitrato-κO)cadmium(II)] top

Crystal data top

[Cd₂(NO₃)₄(C₂₄H₁₆N₆)(CH₄O)₂]	F(000) = 916
M_r = 925.37	D_x = 1.866 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1543 reflections
a = 9.0777 (12) Å	θ = 2.9–29.2°
b = 10.8949 (9) Å	µ = 1.38 mm⁻¹
c = 16.690 (2) Å	T = 298 K
β = 93.847 (10)°	Prism, colorless
V = 1646.9 (3) Å³	0.50 × 0.40 × 0.25 mm
Z = 2

Data collection top

Stoe IPDSII diffractometer	4642 independent reflections
Radiation source: fine-focus sealed tube	4223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.8°, θ_min = 2.9°
rotation method scans	h = −12→8
Absorption correction: numerical Shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)	k = −14→10
T_min = 0.510, T_max = 0.710	l = −22→19
4664 measured reflections

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1202P)² + 2.8103P] where P = (F_o² + 2F_c²)/3
4642 reflections	(Δ/σ)_max = 0.015
239 parameters	Δρ_max = 1.00 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

[Cd₂(NO₃)₄(C₂₄H₁₆N₆)(CH₄O)₂]	V = 1646.9 (3) Å³
M_r = 925.37	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0777 (12) Å	µ = 1.38 mm⁻¹
b = 10.8949 (9) Å	T = 298 K
c = 16.690 (2) Å	0.50 × 0.40 × 0.25 mm
β = 93.847 (10)°

Data collection top

Stoe IPDSII diffractometer	4642 independent reflections
Absorption correction: numerical Shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)	4223 reflections with I > 2σ(I)
T_min = 0.510, T_max = 0.710	R_int = 0.075
4664 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.00 e Å⁻³
4642 reflections	Δρ_min = −0.95 e Å⁻³
239 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 > 2sigma(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	0.38914 (3)	0.18792 (3)	0.167582 (18)	0.02737 (16)
O1	0.5852 (4)	0.0852 (3)	0.2353 (3)	0.0397 (8)
H1B	0.580 (6)	0.001 (5)	0.233 (3)	0.020 (11)*
O2	0.2968 (5)	0.1892 (3)	0.3010 (3)	0.0391 (9)
O3	0.4556 (4)	0.3323 (3)	0.2788 (2)	0.0359 (8)
O4	0.3358 (5)	0.3363 (5)	0.3875 (3)	0.0502 (10)
O5	0.2209 (6)	0.3467 (5)	0.1596 (3)	0.0541 (10)
O6	0.1241 (9)	0.2195 (8)	0.0768 (8)	0.118 (4)
O7	−0.0039 (8)	0.3728 (10)	0.1114 (5)	0.115 (3)
N1	0.2489 (4)	0.0003 (4)	0.1585 (3)	0.0343 (8)
N2	0.4388 (4)	0.0798 (3)	0.0499 (2)	0.0270 (7)
N3	0.5671 (4)	0.2952 (3)	0.0946 (3)	0.0295 (7)
N4	0.3612 (4)	0.2867 (4)	0.3234 (2)	0.0288 (7)
N5	0.1090 (6)	0.3123 (4)	0.1154 (4)	0.0449 (12)
C1	0.1339 (6)	−0.0214 (5)	0.2045 (4)	0.0440 (12)
H1	0.1363	0.0123	0.2558	0.053*
C2	0.0136 (6)	−0.0917 (6)	0.1781 (4)	0.0482 (14)
H2	−0.0620	−0.1068	0.2117	0.058*
C3	0.0071 (5)	−0.1392 (6)	0.1013 (4)	0.0465 (13)
H3	−0.0750	−0.1838	0.0816	0.056*
C4	0.1251 (5)	−0.1196 (5)	0.0536 (3)	0.0365 (10)
H4	0.1232	−0.1502	0.0016	0.044*
C5	0.2455 (4)	−0.0533 (4)	0.0855 (3)	0.0314 (8)
C6	0.3792 (4)	−0.0321 (4)	0.0401 (3)	0.0264 (8)
C7	0.5546 (4)	0.1162 (4)	0.0106 (3)	0.0258 (7)
C8	0.5956 (4)	0.2482 (4)	0.0224 (3)	0.0279 (8)
C9	0.6505 (5)	0.3192 (4)	−0.0380 (3)	0.0319 (10)
H9	0.6588	0.2868	−0.0890	0.038*
C10	0.6926 (5)	0.4390 (4)	−0.0209 (3)	0.0361 (10)
H10	0.7325	0.4875	−0.0599	0.043*
C11	0.6746 (5)	0.4859 (4)	0.0553 (3)	0.0358 (10)
H11	0.7062	0.5648	0.0689	0.043*
C12	0.6086 (5)	0.4124 (4)	0.1104 (3)	0.0324 (9)
H12	0.5920	0.4451	0.1605	0.039*
C13	0.7367 (7)	0.1300 (6)	0.2397 (5)	0.0525 (14)
H13A	0.7409	0.2093	0.2650	0.063*
H13B	0.7702	0.1366	0.1865	0.063*
H13C	0.7990	0.0738	0.2706	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0283 (2)	0.0260 (2)	0.0286 (2)	0.00137 (9)	0.00796 (15)	−0.00333 (9)
O1	0.0364 (16)	0.0306 (16)	0.052 (2)	0.0038 (13)	0.0046 (16)	0.0021 (15)
O2	0.045 (2)	0.0310 (17)	0.043 (2)	−0.0054 (12)	0.0127 (18)	0.0033 (13)
O3	0.0322 (15)	0.0335 (14)	0.043 (2)	−0.0044 (12)	0.0110 (16)	−0.0079 (14)
O4	0.0327 (17)	0.082 (3)	0.037 (2)	−0.0043 (18)	0.0072 (16)	−0.023 (2)
O5	0.056 (2)	0.056 (2)	0.050 (2)	0.018 (2)	−0.002 (2)	−0.004 (2)
O6	0.090 (5)	0.076 (4)	0.179 (11)	0.014 (4)	−0.058 (6)	−0.043 (6)
O7	0.063 (4)	0.176 (8)	0.107 (6)	0.073 (5)	0.014 (4)	0.038 (6)
N1	0.0264 (16)	0.042 (2)	0.0352 (19)	−0.0026 (14)	0.0116 (16)	−0.0054 (16)
N2	0.0235 (14)	0.0275 (15)	0.0303 (17)	0.0017 (12)	0.0046 (14)	−0.0009 (13)
N3	0.0296 (17)	0.0284 (15)	0.0311 (18)	0.0012 (13)	0.0064 (15)	−0.0029 (14)
N4	0.0234 (15)	0.0354 (16)	0.0279 (17)	−0.0004 (13)	0.0047 (14)	−0.0077 (15)
N5	0.051 (2)	0.091 (3)	0.082 (3)	0.0054 (16)	0.002 (2)	0.015 (2)
C1	0.032 (2)	0.053 (3)	0.050 (3)	−0.005 (2)	0.018 (2)	−0.011 (2)
C2	0.031 (2)	0.055 (3)	0.060 (3)	−0.009 (2)	0.021 (2)	−0.015 (3)
C3	0.028 (2)	0.052 (3)	0.061 (3)	−0.009 (2)	0.012 (2)	−0.013 (3)
C4	0.0243 (17)	0.039 (2)	0.047 (3)	0.0025 (16)	0.0053 (18)	−0.012 (2)
C5	0.0228 (16)	0.036 (2)	0.036 (2)	0.0003 (15)	0.0055 (16)	−0.0057 (18)
C6	0.0229 (16)	0.0293 (18)	0.0275 (18)	0.0006 (13)	0.0050 (15)	−0.0047 (15)
C7	0.0219 (15)	0.0279 (17)	0.0282 (18)	0.0002 (14)	0.0050 (15)	−0.0029 (15)
C8	0.0230 (16)	0.0288 (18)	0.033 (2)	0.0007 (14)	0.0063 (15)	−0.0021 (16)
C9	0.0276 (19)	0.032 (2)	0.037 (2)	−0.0010 (14)	0.0117 (19)	−0.0024 (16)
C10	0.034 (2)	0.032 (2)	0.044 (2)	−0.0045 (17)	0.012 (2)	−0.0003 (19)
C11	0.033 (2)	0.0295 (19)	0.046 (3)	−0.0027 (16)	0.009 (2)	−0.0044 (19)
C12	0.0320 (18)	0.0294 (19)	0.036 (2)	0.0036 (15)	0.0055 (18)	−0.0053 (17)
C13	0.044 (3)	0.051 (3)	0.063 (4)	0.003 (2)	0.008 (3)	0.005 (3)

Geometric parameters (Å, º) top

O1—Cd1	2.330 (4)	C4—H4	0.9300
O1—H1B	0.92 (5)	C5—N1	1.349 (6)
O2—Cd1	2.431 (4)	C5—C6	1.492 (5)
O3—Cd1	2.476 (4)	C6—N2	1.340 (5)
O5—Cd1	2.305 (4)	C6—C7ⁱ	1.409 (5)
N1—Cd1	2.407 (4)	C7—N2	1.336 (5)
N2—Cd1	2.359 (4)	C7—C6ⁱ	1.409 (5)
N3—Cd1	2.393 (4)	C7—C8	1.495 (6)
N4—O4	1.234 (5)	C8—N3	1.350 (6)
N4—O2	1.257 (5)	C8—C9	1.389 (6)
N4—O3	1.273 (5)	C9—C10	1.385 (6)
N5—O6	1.211 (10)	C9—H9	0.9300
N5—O7	1.217 (7)	C10—C11	1.390 (7)
N5—O5	1.271 (8)	C10—H10	0.9300
C1—N1	1.357 (6)	C11—C12	1.387 (6)
C1—C2	1.382 (8)	C11—H11	0.9300
C1—H1	0.9300	C12—N3	1.352 (6)
C2—C3	1.380 (9)	C12—H12	0.9300
C2—H2	0.9300	C13—O1	1.457 (7)
C3—C4	1.393 (6)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.385 (6)	C13—H13C	0.9600

O5—Cd1—O1	150.47 (16)	N1—C1—C2	122.5 (5)
O5—Cd1—N2	119.29 (16)	N1—C1—H1	118.8
O1—Cd1—N2	88.94 (13)	C2—C1—H1	118.8
O5—Cd1—N3	94.10 (16)	C3—C2—C1	119.2 (5)
O1—Cd1—N3	87.79 (13)	C3—C2—H2	120.4
N2—Cd1—N3	69.31 (13)	C1—C2—H2	120.4
O5—Cd1—N1	106.73 (17)	C2—C3—C4	119.0 (5)
O1—Cd1—N1	90.37 (14)	C2—C3—H3	120.5
N2—Cd1—N1	69.73 (12)	C4—C3—H3	120.5
N3—Cd1—N1	139.02 (13)	C5—C4—C3	118.5 (5)
O5—Cd1—O2	77.34 (15)	C5—C4—H4	120.7
O1—Cd1—O2	81.82 (14)	C3—C4—H4	120.7
N2—Cd1—O2	149.55 (11)	N1—C5—C4	122.8 (4)
N3—Cd1—O2	138.56 (14)	N1—C5—C6	114.9 (4)
N1—Cd1—O2	81.32 (12)	C4—C5—C6	122.2 (4)
O5—Cd1—O3	72.18 (16)	N2—C6—C7ⁱ	118.7 (3)
O1—Cd1—O3	78.57 (14)	N2—C6—C5	114.5 (3)
N2—Cd1—O3	152.93 (12)	C7ⁱ—C6—C5	126.8 (4)
N3—Cd1—O3	86.13 (13)	N2—C7—C6ⁱ	118.9 (4)
N1—Cd1—O3	133.44 (13)	N2—C7—C8	114.7 (3)
O2—Cd1—O3	52.52 (12)	C6ⁱ—C7—C8	126.3 (3)
C13—O1—Cd1	123.5 (3)	N3—C8—C9	122.4 (4)
C13—O1—H1B	112 (3)	N3—C8—C7	114.9 (3)
Cd1—O1—H1B	115 (4)	C9—C8—C7	122.6 (4)
N4—O2—Cd1	95.5 (3)	C10—C9—C8	118.9 (5)
N4—O3—Cd1	92.9 (2)	C10—C9—H9	120.6
N5—O5—Cd1	108.2 (4)	C8—C9—H9	120.6
C5—N1—C1	117.6 (4)	C9—C10—C11	119.1 (4)
C5—N1—Cd1	113.9 (3)	C9—C10—H10	120.4
C1—N1—Cd1	122.4 (3)	C11—C10—H10	120.4
C7—N2—C6	122.3 (3)	C12—C11—C10	118.5 (4)
C7—N2—Cd1	117.5 (3)	C12—C11—H11	120.7
C6—N2—Cd1	117.3 (3)	C10—C11—H11	120.7
C8—N3—C12	117.7 (4)	N3—C12—C11	122.8 (4)
C8—N3—Cd1	116.4 (3)	N3—C12—H12	118.6
C12—N3—Cd1	123.4 (3)	C11—C12—H12	118.6
O4—N4—O2	121.2 (4)	O1—C13—H13A	109.5
O4—N4—O3	120.5 (4)	O1—C13—H13B	109.5
O2—N4—O3	118.2 (4)	H13A—C13—H13B	109.5
O6—N5—O7	123.2 (9)	O1—C13—H13C	109.5
O6—N5—O5	116.1 (6)	H13A—C13—H13C	109.5
O7—N5—O5	120.6 (8)	H13B—C13—H13C	109.5

N1—C1—C2—C3	−1.9 (10)	C13—O1—Cd1—N3	19.8 (4)
C1—C2—C3—C4	2.8 (10)	C13—O1—Cd1—N1	158.9 (4)
C2—C3—C4—C5	0.4 (9)	C13—O1—Cd1—O2	−119.9 (4)
C3—C4—C5—N1	−4.9 (8)	C13—O1—Cd1—O3	−66.7 (4)
C3—C4—C5—C6	177.5 (5)	C7—N2—Cd1—O5	94.7 (4)
N1—C5—C6—N2	−36.5 (6)	C6—N2—Cd1—O5	−104.3 (4)
C4—C5—C6—N2	141.4 (5)	C7—N2—Cd1—O1	−76.2 (3)
N1—C5—C6—C7ⁱ	143.9 (5)	C6—N2—Cd1—O1	84.8 (3)
C4—C5—C6—C7ⁱ	−38.2 (7)	C7—N2—Cd1—N3	11.8 (3)
N2—C7—C8—N3	31.1 (6)	C6—N2—Cd1—N3	172.8 (4)
C6ⁱ—C7—C8—N3	−152.5 (4)	C7—N2—Cd1—N1	−167.0 (4)
N2—C7—C8—C9	−145.2 (4)	C6—N2—Cd1—N1	−6.0 (3)
C6ⁱ—C7—C8—C9	31.2 (7)	C7—N2—Cd1—O2	−148.0 (3)
N3—C8—C9—C10	7.2 (7)	C6—N2—Cd1—O2	13.0 (5)
C7—C8—C9—C10	−176.8 (5)	C7—N2—Cd1—O3	−14.4 (5)
C8—C9—C10—C11	−2.0 (8)	C6—N2—Cd1—O3	146.6 (3)
C9—C10—C11—C12	−2.9 (8)	C8—N3—Cd1—O5	−114.3 (3)
C10—C11—C12—N3	3.1 (8)	C12—N3—Cd1—O5	47.6 (4)
C4—C5—N1—C1	5.8 (8)	C8—N3—Cd1—O1	95.3 (3)
C6—C5—N1—C1	−176.4 (5)	C12—N3—Cd1—O1	−102.9 (4)
C4—C5—N1—Cd1	−147.4 (4)	C8—N3—Cd1—N2	5.6 (3)
C6—C5—N1—Cd1	30.5 (5)	C12—N3—Cd1—N2	167.4 (4)
C2—C1—N1—C5	−2.4 (9)	C8—N3—Cd1—N1	7.2 (5)
C2—C1—N1—Cd1	148.4 (5)	C12—N3—Cd1—N1	169.1 (4)
C6ⁱ—C7—N2—C6	−3.0 (7)	C8—N3—Cd1—O2	170.3 (3)
C8—C7—N2—C6	173.7 (4)	C12—N3—Cd1—O2	−27.9 (5)
C6ⁱ—C7—N2—Cd1	157.0 (3)	C8—N3—Cd1—O3	173.9 (3)
C8—C7—N2—Cd1	−26.3 (5)	C12—N3—Cd1—O3	−24.2 (4)
C7ⁱ—C6—N2—C7	3.0 (7)	C5—N1—Cd1—O5	102.0 (3)
C5—C6—N2—C7	−176.7 (4)	C1—N1—Cd1—O5	−49.8 (5)
C7ⁱ—C6—N2—Cd1	−157.0 (3)	C5—N1—Cd1—O1	−102.5 (3)
C5—C6—N2—Cd1	23.3 (5)	C1—N1—Cd1—O1	105.8 (5)
C9—C8—N3—C12	−7.0 (7)	C5—N1—Cd1—N2	−13.7 (3)
C7—C8—N3—C12	176.7 (4)	C1—N1—Cd1—N2	−165.5 (5)
C9—C8—N3—Cd1	155.9 (4)	C5—N1—Cd1—N3	−15.4 (5)
C7—C8—N3—Cd1	−20.4 (5)	C1—N1—Cd1—N3	−167.2 (4)
C11—C12—N3—C8	1.7 (7)	C5—N1—Cd1—O2	175.9 (4)
C11—C12—N3—Cd1	−159.9 (4)	C1—N1—Cd1—O2	24.1 (5)
O4—N4—O2—Cd1	171.9 (4)	C5—N1—Cd1—O3	−177.0 (3)
O3—N4—O2—Cd1	−9.3 (5)	C1—N1—Cd1—O3	31.3 (5)
O4—N4—O3—Cd1	−172.1 (4)	N4—O2—Cd1—O5	−71.8 (3)
O2—N4—O3—Cd1	9.1 (5)	N4—O2—Cd1—O1	87.1 (3)
O6—N5—O5—Cd1	−12.9 (9)	N4—O2—Cd1—N2	160.8 (3)
O7—N5—O5—Cd1	169.2 (6)	N4—O2—Cd1—N3	9.9 (4)
N5—O5—Cd1—O1	−154.5 (3)	N4—O2—Cd1—N1	178.8 (3)
N5—O5—Cd1—N2	44.2 (4)	N4—O2—Cd1—O3	5.3 (3)
N5—O5—Cd1—N3	112.8 (4)	N4—O3—Cd1—O5	82.3 (3)
N5—O5—Cd1—N1	−31.5 (4)	N4—O3—Cd1—O1	−93.6 (3)
N5—O5—Cd1—O2	−108.3 (4)	N4—O3—Cd1—N2	−157.7 (3)
N5—O5—Cd1—O3	−162.6 (4)	N4—O3—Cd1—N3	177.9 (3)
C13—O1—Cd1—O5	−74.6 (5)	N4—O3—Cd1—N1	−14.1 (4)
C13—O1—Cd1—N2	89.2 (4)	N4—O3—Cd1—O2	−5.2 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3ⁱⁱ	0.92 (5)	1.87 (5)	2.788 (5)	172

Symmetry code: (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd₂(NO₃)₄(C₂₄H₁₆N₆)(CH₄O)₂]
M_r	925.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.0777 (12), 10.8949 (9), 16.690 (2)
β (°)	93.847 (10)
V (Å³)	1646.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.50 × 0.40 × 0.25

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical Shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.510, 0.710
No. of measured, independent and observed [I > 2σ(I)] reflections	4664, 4642, 4223
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.700

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.171, 1.07
No. of reflections	4642
No. of parameters	239
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.00, −0.95

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

O1—Cd1	2.330 (4)	N1—Cd1	2.407 (4)
O2—Cd1	2.431 (4)	N2—Cd1	2.359 (4)
O3—Cd1	2.476 (4)	N3—Cd1	2.393 (4)
O5—Cd1	2.305 (4)

O5—Cd1—O1	150.47 (16)	O1—Cd1—O2	81.82 (14)
O5—Cd1—N2	119.29 (16)	N2—Cd1—O2	149.55 (11)
O1—Cd1—N2	88.94 (13)	N3—Cd1—O2	138.56 (14)
O5—Cd1—N3	94.10 (16)	N1—Cd1—O2	81.32 (12)
O1—Cd1—N3	87.79 (13)	O5—Cd1—O3	72.18 (16)
N2—Cd1—N3	69.31 (13)	O1—Cd1—O3	78.57 (14)
O5—Cd1—N1	106.73 (17)	N2—Cd1—O3	152.93 (12)
O1—Cd1—N1	90.37 (14)	N3—Cd1—O3	86.13 (13)
N2—Cd1—N1	69.73 (12)	N1—Cd1—O3	133.44 (13)
N3—Cd1—N1	139.02 (13)	O2—Cd1—O3	52.52 (12)
O5—Cd1—O2	77.34 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3ⁱ	0.92 (5)	1.87 (5)	2.788 (5)	172

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

We are grateful to the Science and Research Campus, Islamic Azad University, Poonak, and Shahid Beheshti University for financial support

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