Chimeric supra­molecular synthons in Ph₂Te₂(I₂)Se

Iodination of Ph₂Te₂Se by mol­ecular iodine is directed towards the Te atom and yields {di­iodo­[(phenyl­tellan­yl)selan­yl]-λ⁴-tellan­yl}benzene, PhTeSeTeI₂Ph or C₁₂H₁₀I₂SeTe₂. The mol­ecule can be considered as a chimera of PhTeSeR, PhTeSeTePh and R′TeI₂Ph fragments. The crystal structure features a com­plex inter­play of the supra­molecular synthons Te...π(Ph), Se...Te and I...Te, combining mol­ecules into a three-dimensional framework. Their combination affords long-range supra­molecular synthons which are fused in a way resembling the mythological chimera and could be defined as chimeric supra­molecular synthons. The energies of the inter­molecular inter­actions have also been calculated and analyzed.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

{Diiodo[(phenyltellanyl)selanyl]-λ⁴-tellanyl}benzene

Crystal data

C12H10I2SeTe2	F(000) = 1304
Mr = 742.16	Dx = 3.017 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.980 (3) Å	Cell parameters from 1318 reflections
b = 16.037 (3) Å	θ = 2.9–23.7°
c = 7.8571 (16) Å	µ = 9.56 mm^−1
β = 92.406 (3)°	T = 150 K
V = 1634.1 (6) Å^3	Prism, blackish red
Z = 4	0.1 × 0.05 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	2335 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.081
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan	h = −16→15
Tmin = 0.575, Tmax = 0.746	k = −20→20
12994 measured reflections	l = −10→9
3687 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0235P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
3687 reflections	Δρmax = 2.01 e Å^−3
154 parameters	Δρmin = −1.21 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Suitable X-ray quality crystals of 1 were obtained directly from the reaction mixture (see above). A Bruker APEX II CCD area detector diffractometer equipped with a low-temperature attachment was used for the cell determination and intensity data collection. Empirical absorption corrections was applied using the programs SADABS. Structure was solved by direct methods and refined by least squares method for F² in anisotropic (isotropic for H atoms) approximation in SHELXTL and Olex2 software (Sheldrick, 2015, Dolomanov et al., 2009).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Te1	0.29240 (5)	0.66948 (3)	1.16319 (7)	0.01796 (14)
I2	0.46113 (5)	0.66662 (4)	0.93177 (8)	0.02885 (18)
I1	0.12421 (5)	0.66817 (4)	1.39677 (8)	0.02681 (17)
Te2	0.33187 (5)	0.51436 (4)	1.58207 (7)	0.02262 (17)
Se1	0.42561 (8)	0.57892 (6)	1.34372 (11)	0.0219 (2)
C11	0.1206 (9)	0.3411 (6)	1.3122 (12)	0.031 (3)
H11	0.049700	0.337694	1.291093	0.037*
C5	0.0822 (8)	0.5141 (6)	0.8546 (11)	0.031 (2)
H5	0.018956	0.522549	0.797160	0.038*
C1	0.2239 (8)	0.5681 (5)	1.0257 (10)	0.021 (2)
C6	0.1275 (8)	0.5792 (6)	0.9436 (11)	0.027 (2)
H6	0.094125	0.630419	0.948947	0.032*
C4	0.1276 (8)	0.4374 (6)	0.8482 (10)	0.025 (2)
H4	0.094635	0.393511	0.790924	0.030*
C7	0.2683 (7)	0.4111 (5)	1.4413 (10)	0.017 (2)
C10	0.1857 (8)	0.2807 (6)	1.2480 (11)	0.028 (2)
H10	0.158203	0.236875	1.183308	0.033*
C3	0.2239 (8)	0.4263 (5)	0.9290 (10)	0.021 (2)
H3	0.256653	0.374817	0.923583	0.026*
C12	0.1633 (8)	0.4070 (6)	1.4092 (11)	0.025 (2)
H12	0.120614	0.447974	1.451708	0.030*
C2	0.2720 (7)	0.4922 (5)	1.0186 (10)	0.017 (2)
H2	0.336331	0.484424	1.073081	0.021*
C8	0.3307 (7)	0.3505 (5)	1.3824 (10)	0.020 (2)
H8	0.401028	0.351970	1.410140	0.024*
C9	0.2898 (8)	0.2858 (5)	1.2800 (11)	0.023 (2)
H9	0.333407	0.246568	1.234029	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Te1	0.0218 (4)	0.0133 (3)	0.0185 (3)	−0.0003 (3)	−0.0030 (2)	0.0004 (2)
I2	0.0288 (4)	0.0252 (4)	0.0332 (4)	−0.0042 (3)	0.0088 (3)	0.0015 (3)
I1	0.0258 (4)	0.0273 (4)	0.0276 (3)	0.0012 (3)	0.0043 (3)	−0.0054 (3)
Te2	0.0299 (4)	0.0195 (3)	0.0182 (3)	−0.0002 (3)	−0.0028 (3)	0.0001 (3)
Se1	0.0261 (6)	0.0180 (5)	0.0211 (5)	−0.0034 (4)	−0.0073 (4)	0.0028 (4)
C11	0.034 (7)	0.024 (6)	0.034 (6)	−0.017 (5)	−0.004 (5)	0.012 (5)
C5	0.021 (6)	0.042 (7)	0.030 (6)	−0.011 (5)	−0.011 (4)	−0.002 (5)
C1	0.028 (6)	0.015 (5)	0.020 (5)	−0.011 (4)	0.006 (4)	−0.005 (4)
C6	0.024 (6)	0.021 (5)	0.034 (6)	0.008 (5)	−0.007 (5)	−0.001 (4)
C4	0.033 (7)	0.021 (5)	0.018 (5)	−0.006 (5)	−0.011 (4)	−0.007 (4)
C7	0.018 (6)	0.011 (4)	0.020 (5)	−0.008 (4)	0.000 (4)	0.006 (4)
C10	0.040 (8)	0.028 (6)	0.015 (5)	−0.005 (5)	0.004 (5)	0.002 (4)
C3	0.043 (7)	0.007 (4)	0.014 (5)	0.000 (4)	0.007 (4)	0.003 (3)
C12	0.027 (6)	0.024 (5)	0.025 (5)	0.001 (5)	0.008 (4)	0.005 (4)
C2	0.023 (6)	0.012 (4)	0.017 (4)	−0.001 (4)	−0.003 (4)	0.000 (4)
C8	0.017 (6)	0.020 (5)	0.022 (5)	−0.008 (4)	−0.001 (4)	0.005 (4)
C9	0.030 (7)	0.021 (5)	0.017 (5)	0.002 (4)	−0.002 (4)	0.003 (4)

Geometric parameters (Å, º)

Te1—I2	2.9051 (10)	C6—H6	0.9300
Te1—I1	2.9105 (10)	C4—H4	0.9300
Te1—Se1	2.6277 (12)	C4—C3	1.390 (13)
Te1—C1	2.126 (8)	C7—C12	1.377 (13)
Te2—Se1	2.5002 (11)	C7—C8	1.358 (12)
Te2—C7	2.138 (8)	C10—H10	0.9300
C11—H11	0.9300	C10—C9	1.367 (14)
C11—C10	1.393 (14)	C3—H3	0.9300
C11—C12	1.404 (13)	C3—C2	1.402 (11)
C5—H5	0.9300	C12—H12	0.9300
C5—C6	1.375 (12)	C2—H2	0.9300
C5—C4	1.365 (13)	C8—H8	0.9300
C1—C6	1.395 (13)	C8—C9	1.404 (12)
C1—C2	1.371 (12)	C9—H9	0.9300
I2—Te1—I1	178.64 (3)	C3—C4—H4	120.7
Se1—Te1—I2	80.38 (3)	C12—C7—Te2	119.3 (7)
Se1—Te1—I1	98.61 (3)	C8—C7—Te2	120.5 (7)
C1—Te1—I2	88.9 (2)	C8—C7—C12	120.2 (8)
C1—Te1—I1	90.4 (2)	C11—C10—H10	119.9
C1—Te1—Se1	95.9 (3)	C9—C10—C11	120.1 (9)
C7—Te2—Se1	97.1 (2)	C9—C10—H10	119.9
Te2—Se1—Te1	107.66 (5)	C4—C3—H3	119.8
C10—C11—H11	120.4	C4—C3—C2	120.4 (8)
C10—C11—C12	119.3 (10)	C2—C3—H3	119.8
C12—C11—H11	120.4	C11—C12—H12	120.0
C6—C5—H5	119.1	C7—C12—C11	120.0 (9)
C4—C5—H5	119.1	C7—C12—H12	120.0
C4—C5—C6	121.8 (10)	C1—C2—C3	119.7 (9)
C6—C1—Te1	119.0 (7)	C1—C2—H2	120.1
C2—C1—Te1	121.2 (7)	C3—C2—H2	120.1
C2—C1—C6	119.8 (8)	C7—C8—H8	119.8
C5—C6—C1	119.6 (9)	C7—C8—C9	120.5 (9)
C5—C6—H6	120.2	C9—C8—H8	119.8
C1—C6—H6	120.2	C10—C9—C8	119.8 (9)
C5—C4—H4	120.7	C10—C9—H9	120.1
C5—C4—C3	118.7 (8)	C8—C9—H9	120.1