Di-μ-iodido-bis-(iodido-{methyl 4-[(pyridin-2-yl-methyl-idene)amino]-benzoate-κ(2) N,N'}cadmium).

The complete binuclear molecule of the title compound, [Cd2I4(C14H12N2O2)2], is generated by the application of a centre of inversion. The Cd-I bond lengths of the central core are close and uniformly longer than the exocyclic Cd-I bond. The coordination sphere of the Cd(II) atom is completed by two N atoms of a chelating methyl 4-[(pyridin-2-yl-methyl-idene)amino]-benzoate ligand, and is based on a square pyramid with the terminal I atom in the apical position. The three-dimensional crystal packing is stabilized by C-H⋯O and C-H⋯π inter-actions, each involving the pyridine ring.

Related literature

For spectroscopic, biological and structural studies of zinc triad elements with (E)-N-(pyridin-2-yl­methyl­idene)aryl­amine ligands, see: Basu Baul, Kundu, Höpfl et al. (2013 ▶); Basu Baul, Kundu, Linden et al. (2013 ▶); Basu Baul, Kundu, Mitra et al. (2013 ▶). For additional structural analysis, see: Addison et al. (1984 ▶).

Experimental

Crystal data

[Cd2I4(C14H12N2O2)2]

M = 1212.91

Triclinic,

a = 8.4883 (3) Å

b = 9.3677 (5) Å

c = 10.9029 (5) Å

α = 109.516 (5)°

β = 95.868 (3)°

γ = 90.242 (4)°

V = 812.18 (6) Å3

Z = 1

Mo Kα radiation

μ = 5.15 mm−1

T = 100 K

0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.698, T max = 1.000

11886 measured reflections

3738 independent reflections

3374 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.050

S = 1.00

3738 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −1.04 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) general, I. DOI: 10.1107/S160053681302905X/hg5357sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302905X/hg5357Isup2.hkl

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

[Cd2I4(C14H12N2O2)2]	Z = 1
Mr = 1212.91	F(000) = 560
Triclinic, P1	Dx = 2.480 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4883 (3) Å	Cell parameters from 5933 reflections
b = 9.3677 (5) Å	θ = 2.3–27.5°
c = 10.9029 (5) Å	µ = 5.15 mm−1
α = 109.516 (5)°	T = 100 K
β = 95.868 (3)°	Prism, yellow
γ = 90.242 (4)°	0.20 × 0.15 × 0.10 mm
V = 812.18 (6) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3738 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3374 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.031
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −10→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −12→12
Tmin = 0.698, Tmax = 1.000	l = −14→14
11886 measured reflections

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) = 0.050	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.021P)2 + 0.5485P] where P = (Fo2 + 2Fc2)/3
3738 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −1.04 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
I1	0.36407 (2)	0.52109 (2)	0.344025 (19)	0.01447 (6)
I2	0.54922 (2)	0.97175 (3)	0.69338 (2)	0.01683 (6)
Cd	0.39702 (2)	0.69721 (3)	0.61836 (2)	0.01149 (6)
N1	0.2891 (3)	0.6752 (3)	0.8000 (2)	0.0118 (5)
N2	0.1161 (3)	0.7293 (3)	0.5962 (2)	0.0110 (5)
O1	−0.1491 (3)	0.9351 (3)	0.1141 (2)	0.0162 (5)
O2	−0.3079 (3)	0.7290 (3)	0.0766 (2)	0.0206 (5)
C1	0.3737 (4)	0.6588 (4)	0.9039 (3)	0.0153 (7)
H1	0.4858	0.6579	0.9063	0.018*
C2	0.3043 (4)	0.6428 (4)	1.0096 (3)	0.0150 (7)
H2	0.3682	0.6340	1.0833	0.018*
C3	0.1418 (4)	0.6401 (4)	1.0051 (3)	0.0157 (7)
H3	0.0915	0.6254	1.0741	0.019*
C4	0.0520 (4)	0.6593 (4)	0.8977 (3)	0.0139 (7)
H4	−0.0604	0.6582	0.8924	0.017*
C5	0.1304 (4)	0.6800 (4)	0.7980 (3)	0.0123 (6)
C6	0.0422 (4)	0.7113 (4)	0.6870 (3)	0.0119 (6)
H6	−0.0697	0.7181	0.6826	0.014*
C7	0.0294 (3)	0.7576 (4)	0.4877 (3)	0.0107 (6)
C8	−0.1235 (4)	0.6954 (4)	0.4383 (3)	0.0130 (6)
H8	−0.1757	0.6374	0.4800	0.016*
C9	−0.1987 (4)	0.7191 (4)	0.3279 (3)	0.0153 (7)
H9	−0.3021	0.6761	0.2933	0.018*
C10	−0.1227 (3)	0.8059 (4)	0.2677 (3)	0.0103 (6)
C11	0.0284 (3)	0.8706 (4)	0.3191 (3)	0.0115 (6)
H11	0.0785	0.9326	0.2798	0.014*
C12	0.1058 (3)	0.8445 (4)	0.4279 (3)	0.0114 (6)
H12	0.2101	0.8857	0.4613	0.014*
C13	−0.2045 (4)	0.8179 (4)	0.1441 (3)	0.0135 (7)
C14	−0.2324 (4)	0.9537 (4)	−0.0024 (3)	0.0175 (7)
H14A	−0.2363	0.8575	−0.0752	0.026*
H14B	−0.1767	1.0318	−0.0248	0.026*
H14C	−0.3406	0.9843	0.0144	0.026*

	U11	U22	U33	U12	U13	U23
I1	0.01401 (11)	0.01747 (12)	0.01205 (11)	0.00245 (8)	0.00116 (8)	0.00518 (9)
I2	0.01733 (11)	0.01644 (12)	0.01742 (11)	−0.00593 (9)	−0.00164 (8)	0.00774 (9)
Cd	0.01011 (11)	0.01394 (13)	0.01083 (12)	−0.00150 (9)	0.00068 (9)	0.00488 (10)
N1	0.0126 (13)	0.0116 (14)	0.0107 (13)	−0.0020 (11)	0.0000 (10)	0.0034 (11)
N2	0.0121 (12)	0.0113 (14)	0.0104 (13)	0.0009 (11)	0.0005 (10)	0.0050 (11)
O1	0.0210 (12)	0.0152 (13)	0.0131 (11)	−0.0027 (10)	−0.0055 (9)	0.0078 (10)
O2	0.0213 (12)	0.0181 (14)	0.0211 (13)	−0.0059 (10)	−0.0088 (10)	0.0084 (11)
C1	0.0165 (16)	0.0139 (17)	0.0142 (16)	−0.0020 (13)	−0.0026 (13)	0.0043 (14)
C2	0.0225 (17)	0.0125 (17)	0.0108 (15)	−0.0006 (13)	−0.0015 (13)	0.0058 (14)
C3	0.0226 (17)	0.0133 (17)	0.0139 (16)	−0.0012 (13)	0.0035 (13)	0.0076 (14)
C4	0.0133 (15)	0.0137 (17)	0.0145 (16)	0.0003 (13)	0.0029 (12)	0.0041 (14)
C5	0.0137 (15)	0.0115 (17)	0.0116 (15)	−0.0002 (12)	0.0019 (12)	0.0037 (13)
C6	0.0109 (15)	0.0113 (16)	0.0130 (15)	−0.0003 (12)	0.0006 (12)	0.0035 (13)
C7	0.0117 (15)	0.0106 (16)	0.0086 (14)	0.0021 (12)	−0.0001 (12)	0.0020 (13)
C8	0.0128 (15)	0.0144 (17)	0.0132 (15)	−0.0030 (13)	0.0006 (12)	0.0065 (14)
C9	0.0107 (15)	0.0173 (18)	0.0169 (16)	−0.0026 (13)	−0.0014 (13)	0.0052 (14)
C10	0.0117 (14)	0.0095 (16)	0.0090 (14)	0.0003 (12)	−0.0006 (12)	0.0024 (13)
C11	0.0123 (15)	0.0095 (16)	0.0127 (15)	0.0021 (12)	0.0040 (12)	0.0030 (13)
C12	0.0067 (14)	0.0132 (17)	0.0134 (15)	−0.0001 (12)	0.0000 (12)	0.0036 (13)
C13	0.0138 (15)	0.0134 (17)	0.0126 (15)	0.0019 (13)	−0.0006 (13)	0.0040 (14)
C14	0.0246 (17)	0.0163 (18)	0.0125 (16)	0.0001 (14)	−0.0046 (14)	0.0080 (14)

I1—Cd	2.8765 (4)	C4—C5	1.397 (4)
I1—Cdi	2.9813 (3)	C4—H4	0.9500
I2—Cd	2.7023 (4)	C5—C6	1.471 (4)
Cd—N1	2.333 (2)	C6—H6	0.9500
Cd—N2	2.402 (2)	C7—C12	1.394 (4)
Cd—I1i	2.9813 (3)	C7—C8	1.399 (4)
N1—C1	1.332 (4)	C8—C9	1.388 (4)
N1—C5	1.346 (4)	C8—H8	0.9500
N2—C6	1.280 (4)	C9—C10	1.396 (4)
N2—C7	1.430 (4)	C9—H9	0.9500
O1—C13	1.342 (4)	C10—C11	1.395 (4)
O1—C14	1.452 (4)	C10—C13	1.491 (4)
O2—C13	1.207 (4)	C11—C12	1.390 (4)
C1—C2	1.396 (4)	C11—H11	0.9500
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.375 (5)	C14—H14A	0.9800
C2—H2	0.9500	C14—H14B	0.9800
C3—C4	1.394 (4)	C14—H14C	0.9800
C3—H3	0.9500
Cd—I1—Cdi	92.716 (9)	C4—C5—C6	121.0 (3)
N1—Cd—N2	70.33 (8)	N2—C6—C5	120.1 (3)
N1—Cd—I2	107.66 (7)	N2—C6—H6	119.9
N2—Cd—I2	109.09 (6)	C5—C6—H6	119.9
N1—Cd—I1	134.10 (7)	C12—C7—C8	120.5 (3)
N2—Cd—I1	87.44 (6)	C12—C7—N2	117.5 (3)
I2—Cd—I1	117.588 (10)	C8—C7—N2	122.0 (3)
N1—Cd—I1i	86.88 (6)	C9—C8—C7	119.6 (3)
N2—Cd—I1i	141.81 (6)	C9—C8—H8	120.2
I2—Cd—I1i	106.827 (10)	C7—C8—H8	120.2
I1—Cd—I1i	87.284 (9)	C8—C9—C10	120.1 (3)
C1—N1—C5	118.7 (3)	C8—C9—H9	119.9
C1—N1—Cd	124.5 (2)	C10—C9—H9	119.9
C5—N1—Cd	116.87 (19)	C11—C10—C9	120.1 (3)
C6—N2—C7	119.8 (3)	C11—C10—C13	122.2 (3)
C6—N2—Cd	115.35 (19)	C9—C10—C13	117.6 (3)
C7—N2—Cd	124.74 (18)	C12—C11—C10	120.1 (3)
C13—O1—C14	114.2 (2)	C12—C11—H11	120.0
N1—C1—C2	122.7 (3)	C10—C11—H11	120.0
N1—C1—H1	118.6	C11—C12—C7	119.6 (3)
C2—C1—H1	118.6	C11—C12—H12	120.2
C3—C2—C1	118.8 (3)	C7—C12—H12	120.2
C3—C2—H2	120.6	O2—C13—O1	123.6 (3)
C1—C2—H2	120.6	O2—C13—C10	123.2 (3)
C2—C3—C4	119.0 (3)	O1—C13—C10	113.2 (3)
C2—C3—H3	120.5	O1—C14—H14A	109.5
C4—C3—H3	120.5	O1—C14—H14B	109.5
C3—C4—C5	118.8 (3)	H14A—C14—H14B	109.5
C3—C4—H4	120.6	O1—C14—H14C	109.5
C5—C4—H4	120.6	H14A—C14—H14C	109.5
N1—C5—C4	121.9 (3)	H14B—C14—H14C	109.5
N1—C5—C6	117.1 (3)
Cdi—I1—Cd—N1	−83.00 (8)	Cd—N1—C5—C6	−5.0 (4)
Cdi—I1—Cd—N2	−142.16 (6)	C3—C4—C5—N1	3.0 (5)
Cdi—I1—Cd—I2	107.590 (12)	C3—C4—C5—C6	−175.7 (3)
Cdi—I1—Cd—I1i	0.0	C7—N2—C6—C5	179.1 (3)
N2—Cd—N1—C1	−175.4 (3)	Cd—N2—C6—C5	2.6 (4)
I2—Cd—N1—C1	−70.8 (3)	N1—C5—C6—N2	1.5 (5)
I1—Cd—N1—C1	119.0 (2)	C4—C5—C6—N2	−179.7 (3)
I1i—Cd—N1—C1	35.8 (3)	C6—N2—C7—C12	150.0 (3)
N2—Cd—N1—C5	4.5 (2)	Cd—N2—C7—C12	−33.8 (4)
I2—Cd—N1—C5	109.0 (2)	C6—N2—C7—C8	−32.9 (5)
I1—Cd—N1—C5	−61.1 (2)	Cd—N2—C7—C8	143.3 (2)
I1i—Cd—N1—C5	−144.3 (2)	C12—C7—C8—C9	0.8 (5)
N1—Cd—N2—C6	−3.7 (2)	N2—C7—C8—C9	−176.2 (3)
I2—Cd—N2—C6	−106.2 (2)	C7—C8—C9—C10	−0.7 (5)
I1—Cd—N2—C6	135.4 (2)	C8—C9—C10—C11	−0.8 (5)
I1i—Cd—N2—C6	53.1 (3)	C8—C9—C10—C13	175.7 (3)
N1—Cd—N2—C7	−180.0 (3)	C9—C10—C11—C12	2.2 (5)
I2—Cd—N2—C7	77.5 (2)	C13—C10—C11—C12	−174.0 (3)
I1—Cd—N2—C7	−40.9 (2)	C10—C11—C12—C7	−2.1 (5)
I1i—Cd—N2—C7	−123.2 (2)	C8—C7—C12—C11	0.6 (5)
C5—N1—C1—C2	1.5 (5)	N2—C7—C12—C11	177.7 (3)
Cd—N1—C1—C2	−178.6 (2)	C14—O1—C13—O2	4.4 (4)
N1—C1—C2—C3	1.7 (5)	C14—O1—C13—C10	−177.0 (2)
C1—C2—C3—C4	−2.5 (5)	C11—C10—C13—O2	156.5 (3)
C2—C3—C4—C5	0.2 (5)	C9—C10—C13—O2	−19.9 (5)
C1—N1—C5—C4	−3.9 (5)	C11—C10—C13—O1	−22.1 (4)
Cd—N1—C5—C4	176.3 (3)	C9—C10—C13—O1	161.5 (3)
C1—N1—C5—C6	174.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ii	0.95	2.34	3.066 (4)	133
C14—H14B···Cg1iii	0.98	2.79	3.416 (4)	123

Table 1

Selected bond lengths (Å)

I1—Cd	2.8765 (4)
I1—Cdi	2.9813 (3)
I2—Cd	2.7023 (4)
Cd—N1	2.333 (2)
Cd—N2	2.402 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C1–C5 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ii	0.95	2.34	3.066 (4)	133
C14—H14B⋯Cg1iii	0.98	2.79	3.416 (4)	123

Symmetry codes: (ii) ; (iii) .