Bis(2,6-diiso­propyl­phen­yl) tel­lur­one: a well-defined monomeric diorganotel­lur­one without cocrystallized solvents and without stabilizing intramolecular contacts

Only two crystal structures of diorganotel­lur­ones have been reported to date, both of which contain cocrystallized solvents and one of which is stabilized by intra­molecular Te—N secondary bonding interactions. This work describes the crystal structure of bis­(2,6-diiso­propyl­phen­yl) tel­lur­one, (C₁₂H₁₇)₂TeO₂ or C₂₄H₃₄O₂Te, the first well-defined diorganotel­lur­one without cocrystallized solvents and without stabilizing intramolecular contacts. The mol­ecule has crystallographic twofold symmetry, with half the mol­ecule as the asymmetric unit. The mol­ecular structure is com­pared to previously reported tel­lur­ones and those com­puted at the density functional theory DFT/B3PW91 level. The mol­ecules form two-dimensional layers as a result of a weak inter­molecular hydrogen-bonding network. The layers are then stacked in an anti­parallel manner to form the crystal packing structure. The Hirshfeld surface analysis was employed to visualize and qu­antify the inter­molecular contacts in the mol­ecular crystal structure, and the contribution of O...H and H...H inter­actions was found to be the dominating factor.

Computing details

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis(2,6-diisopropylphenyl) tellurone

Crystal data

C24H34O2Te	Dx = 1.354 Mg m^−3
Mr = 482.11	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 8824 reflections
a = 9.3633 (3) Å	θ = 2.8–29.6°
b = 14.2339 (5) Å	µ = 1.27 mm^−1
c = 17.7479 (5) Å	T = 108 K
V = 2365.37 (13) Å^3	Prism, clear light colourless
Z = 4	0.30 × 0.25 × 0.20 mm
F(000) = 984

Data collection

Rigaku Saturn724+ (2x2 bin mode) diffractometer	2348 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	Rint = 0.053
profile data from ω–scans	θmax = 29.3°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −12→12
Tmin = 0.818, Tmax = 1.000	k = −19→16
21761 measured reflections	l = −22→24
2971 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.009P)^2 + 2.7225P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
2971 reflections	Δρmax = 0.54 e Å^−3
127 parameters	Δρmin = −1.04 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq
Te1	0.500000	0.53742 (2)	0.750000	0.00967 (6)
C10	0.6523 (2)	0.70236 (15)	0.84991 (11)	0.0158 (4)
H10	0.583709	0.649197	0.856669	0.019*
C3	0.8157 (2)	0.69996 (15)	0.62209 (12)	0.0187 (5)
H3	0.856198	0.700172	0.573005	0.022*
C9	0.6527 (3)	0.5808 (2)	0.50988 (14)	0.0379 (7)
H9A	0.566523	0.619365	0.514888	0.057*
H9B	0.632229	0.526568	0.477602	0.057*
H9C	0.729227	0.618348	0.487286	0.057*
C5	0.7956 (2)	0.77154 (14)	0.74427 (13)	0.0184 (4)
H5	0.822371	0.819981	0.778276	0.022*
C6	0.7021 (2)	0.70135 (14)	0.76827 (11)	0.0146 (4)
O1	0.42877 (17)	0.46605 (10)	0.67467 (8)	0.0171 (3)
C1	0.6651 (2)	0.63136 (13)	0.71543 (12)	0.0127 (4)
C12	0.7792 (3)	0.68515 (18)	0.90270 (13)	0.0250 (5)
H12A	0.823966	0.624878	0.890237	0.038*
H12B	0.745638	0.683768	0.954985	0.038*
H12C	0.849184	0.735792	0.896628	0.038*
C7	0.6995 (3)	0.54663 (16)	0.58752 (11)	0.0198 (5)
H7	0.622176	0.505677	0.608286	0.024*
C11	0.5734 (3)	0.79367 (16)	0.86969 (13)	0.0247 (5)
H11A	0.638093	0.847183	0.863096	0.037*
H11B	0.541189	0.791052	0.922176	0.037*
H11C	0.490671	0.801042	0.836407	0.037*
C2	0.7233 (2)	0.62752 (15)	0.64246 (11)	0.0149 (4)
C4	0.8500 (2)	0.77180 (15)	0.67175 (13)	0.0200 (5)
H4	0.910993	0.821341	0.655928	0.024*
C8	0.8368 (4)	0.4881 (2)	0.58284 (18)	0.0458 (8)
H8A	0.821057	0.434007	0.549748	0.069*
H8B	0.862889	0.466090	0.633303	0.069*
H8C	0.914138	0.526958	0.562475	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Te1	0.01162 (9)	0.00776 (9)	0.00963 (9)	0.000	0.00042 (7)	0.000
C10	0.0130 (10)	0.0162 (10)	0.0181 (10)	0.0010 (9)	−0.0037 (8)	−0.0068 (8)
C3	0.0168 (11)	0.0198 (11)	0.0193 (10)	−0.0030 (9)	0.0015 (9)	0.0047 (9)
C9	0.0498 (19)	0.0453 (16)	0.0185 (12)	−0.0211 (14)	−0.0036 (12)	0.0009 (11)
C5	0.0163 (11)	0.0134 (9)	0.0254 (11)	−0.0014 (8)	−0.0067 (9)	−0.0030 (9)
C6	0.0128 (10)	0.0127 (9)	0.0183 (10)	0.0025 (8)	−0.0039 (8)	−0.0019 (7)
O1	0.0204 (8)	0.0156 (7)	0.0152 (7)	−0.0051 (6)	−0.0006 (6)	−0.0054 (6)
C1	0.0125 (10)	0.0099 (9)	0.0158 (9)	−0.0033 (8)	−0.0033 (8)	0.0022 (8)
C12	0.0223 (13)	0.0316 (13)	0.0211 (11)	0.0080 (11)	−0.0076 (10)	−0.0055 (10)
C7	0.0233 (12)	0.0218 (11)	0.0143 (10)	−0.0095 (10)	0.0053 (9)	−0.0023 (8)
C11	0.0212 (13)	0.0249 (12)	0.0281 (12)	0.0057 (10)	−0.0029 (10)	−0.0116 (10)
C2	0.0149 (11)	0.0144 (10)	0.0153 (9)	−0.0001 (9)	−0.0022 (8)	0.0005 (8)
C4	0.0141 (11)	0.0156 (10)	0.0302 (12)	−0.0041 (9)	−0.0040 (9)	0.0056 (9)
C8	0.0439 (18)	0.0379 (16)	0.0557 (19)	0.0092 (14)	−0.0019 (15)	−0.0271 (14)

Geometric parameters (Å, º)

Te1—O1	1.8067 (14)	C5—C4	1.384 (3)
Te1—O1^i	1.8067 (14)	C6—C1	1.411 (3)
Te1—C1	2.134 (2)	C1—C2	1.406 (3)
Te1—C1^i	2.134 (2)	C12—H12A	0.9800
C10—H10	1.0000	C12—H12B	0.9800
C10—C6	1.522 (3)	C12—H12C	0.9800
C10—C12	1.533 (3)	C7—H7	1.0000
C10—C11	1.536 (3)	C7—C2	1.525 (3)
C3—H3	0.9500	C7—C8	1.534 (4)
C3—C2	1.394 (3)	C11—H11A	0.9800
C3—C4	1.388 (3)	C11—H11B	0.9800
C9—H9A	0.9800	C11—H11C	0.9800
C9—H9B	0.9800	C4—H4	0.9500
C9—H9C	0.9800	C8—H8A	0.9800
C9—C7	1.526 (3)	C8—H8B	0.9800
C5—H5	0.9500	C8—H8C	0.9800
C5—C6	1.395 (3)
O1—Te1—O1^i	111.57 (9)	C10—C12—H12A	109.5
O1—Te1—C1	114.02 (7)	C10—C12—H12B	109.5
O1—Te1—C1^i	107.31 (7)	C10—C12—H12C	109.5
O1^i—Te1—C1	107.32 (8)	H12A—C12—H12B	109.5
O1^i—Te1—C1^i	114.02 (7)	H12A—C12—H12C	109.5
C1—Te1—C1^i	102.40 (11)	H12B—C12—H12C	109.5
C6—C10—H10	107.7	C9—C7—H7	108.1
C6—C10—C12	110.07 (18)	C9—C7—C8	111.4 (2)
C6—C10—C11	111.89 (18)	C2—C7—C9	112.27 (19)
C12—C10—H10	107.7	C2—C7—H7	108.1
C12—C10—C11	111.62 (18)	C2—C7—C8	108.77 (19)
C11—C10—H10	107.7	C8—C7—H7	108.1
C2—C3—H3	119.2	C10—C11—H11A	109.5
C4—C3—H3	119.2	C10—C11—H11B	109.5
C4—C3—C2	121.6 (2)	C10—C11—H11C	109.5
H9A—C9—H9B	109.5	H11A—C11—H11B	109.5
H9A—C9—H9C	109.5	H11A—C11—H11C	109.5
H9B—C9—H9C	109.5	H11B—C11—H11C	109.5
C7—C9—H9A	109.5	C3—C2—C1	116.79 (19)
C7—C9—H9B	109.5	C3—C2—C7	118.92 (19)
C7—C9—H9C	109.5	C1—C2—C7	124.15 (19)
C6—C5—H5	119.4	C3—C4—H4	119.9
C4—C5—H5	119.4	C5—C4—C3	120.2 (2)
C4—C5—C6	121.11 (19)	C5—C4—H4	119.9
C5—C6—C10	118.42 (18)	C7—C8—H8A	109.5
C5—C6—C1	117.18 (19)	C7—C8—H8B	109.5
C1—C6—C10	124.33 (19)	C7—C8—H8C	109.5
C6—C1—Te1	115.41 (15)	H8A—C8—H8B	109.5
C2—C1—Te1	121.42 (15)	H8A—C8—H8C	109.5
C2—C1—C6	122.97 (19)	H8B—C8—H8C	109.5
Te1—C1—C2—C3	171.21 (15)	C12—C10—C6—C5	−65.0 (3)
Te1—C1—C2—C7	−13.1 (3)	C12—C10—C6—C1	112.0 (2)
C10—C6—C1—Te1	11.3 (3)	C11—C10—C6—C5	59.7 (3)
C10—C6—C1—C2	−173.9 (2)	C11—C10—C6—C1	−123.3 (2)
C9—C7—C2—C3	−54.1 (3)	C2—C3—C4—C5	1.9 (3)
C9—C7—C2—C1	130.3 (2)	C4—C3—C2—C1	0.8 (3)
C5—C6—C1—Te1	−171.71 (15)	C4—C3—C2—C7	−175.1 (2)
C5—C6—C1—C2	3.2 (3)	C4—C5—C6—C10	176.9 (2)
C6—C5—C4—C3	−2.1 (3)	C4—C5—C6—C1	−0.4 (3)
C6—C1—C2—C3	−3.4 (3)	C8—C7—C2—C3	69.7 (3)
C6—C1—C2—C7	172.3 (2)	C8—C7—C2—C1	−106.0 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	1.00	2.23	3.183 (3)	158
C4^ii—H4^ii···O1	0.95	2.57	3.455 (3)	155
C5^iii—H5^iii···O1	0.95	2.45	3.360 (3)	160

Symmetry codes: (ii) x+1/2, y+1/2, −z+3/2; (iii) −x+3/2, y+1/2, z.