The first crystal structures of six- and seven-membered tellurium- and nitro­gen-containing (Te-N) heterocycles: 2H-1,4-benzo­tellurazin-3(4H)-one and 2,3-di­hydro-1,5-benzo­tellurazepin-4(5H)-one

There is a paucity of data concerning the structures of six- and seven-membered tellurium- and nitro­gen-containing (Te-N) heterocycles. The title compounds, C₈H₇NOTe, (I), and C₉H₉NOTe, (II), represent the first structurally characterized members of their respective classes. Both crystallize with two independent mol­ecules in the asymmetric unit. When compared to their sulfur analogs, they exhibit slightly greater deviations from planarity to accommodate the larger chalcogenide atom, with (II) adopting a pronounced twist-boat conformation. The C-Te-C angles of 85.49 (15) and 85.89 (15)° for the two independent mol­ecules of (I) were found to be somewhat smaller than those of 97.4 (2) and 97.77 (19)° for the two independent mol­ecules of (II). The C-Te bond lengths [2.109 (4)-2.158 (5) Å] are in good agreement with those predicted by the covalent radii. Inter­molecular N-H...O hydrogen bonding in (I) forms centrosymmetric R₂²(8) dimers, while that in (II) forms chains. In addition, inter­molecular Te...O contacts [3.159 (3)-3.200 (3) Å] exist in (I).

S1. Introduction

There is a paucity of data concerning the structures of six-membered tellurium- and nitro­gen-containing (Te—N) heterocycles. The few reported compounds comprise a small number of benzotellurazine derivatives (Detty & O'Regan, 1994). Of these, only 10H-phenotellurazine (Junk & Irgolic, 1989) and 1,1-di­chloro-1,1-di­hydro-2H-1,4-benzotellurazin-3(4H)-one (McMullen et al., 2013) were characterized by X-ray crystallography. Even fewer seven-membered Te—N heterocycles are known. The preparation of 2H-1,4-benzotellurazin-3(4H)-one, (I), was reported twice (Sadekov et al., 1993; McMullen et al., 2013), but no structural parameters were published. In addition, 11-(4-methyl­phenyl)­dibenzo[b,f][1,4]tellurazepine was prepared (Ladatko et al., 1987) but not structurally characterized. In contrast, benzo­thia­zinones and benzo­thia­zepines are well established, the latter being of importance as calcium-channel regulators (Mohacsi & O'Brien, 1991; Rampe & Tiggle, 1993).

We report here the structures of two tellurium-containing compounds, namely (I) and 2,3-di­hydro-1,5-benzotellurazepin-4(5H)-one, (II). Structural characterizations of the sulfur analogs of both (I) and (II) are reported in the literature (Rajnikant et al., 2004; Qin & Zhao, 2006).

S2. Experimental

S2.1. Synthesis and crystallization

S2.1.1. Preparation of (1)

The synthesis of (I) was reported previously (McMullen et al., 2013). Well-formed crystals were obtained by open air evaporation of a solution in di­chloro­methane.

S2.1.2. Preparation of (2)

A 25 ml Erlenmeyer flask was charged with bis­(2-amino­phenyl) ditelluride (250 mg, 0.57 mmol) prepared according to the published of McMullen et al. (2013), pyridine (90 mg, 1.14 mmol) and di­chloro­methane (4 ml). A solution of 3-bromo­propanoyl chloride (145 mg, 1.14 mmol) in di­chloro­methane (0.5 ml) was added with a pipette and the mixture set aside for 4 h. After this time, a precipitate of bis­[2-(3-chloro­propionamido)­phenyl] ditelluride had formed, which was collected by filtration and washed with methanol (1 ml). The damp crude solid was suspended in methanol (5 ml), placed in a 25 ml round-bottomed flask with magnetic stirring and a reflux condenser, heated to reflux, and sodium borohydride added through the condenser until the red color had faded (approximately 50 mg NaBH₄ consumed). Heating was discontinued, the flask content diluted with water (5 ml) and refrigerated for 1 h. The crude product was filtered and washed with cold methanol (approximately 1 ml). It was taken up in hot ethanol (8 ml), filtered hot though a cotton plug and placed in a freezer to crystallize. Recrystallization from ethanol furnished off-white crystals (yield 87 mg, 27.8%; m.p. 494–495 K). ¹H NMR (CDCl₃): δ 2.74 (triplet, 2H), 3.48 (triplet, 2H), 7.03 (triplet, 1H), 7.12 (doublet, 1H), 7.36 (triplet, 1H), 7.89 (triplet, 1H), 8.12 (broad singlet, 1H). ¹³C NMR (CDCl₃): δ 2.80, 34.39, 109.84, 123.86, 127.14, 130.44, 140.91, 143.06, 174.69. The compound oxidizes slowly in solution. A sample suitable for X-ray crystallography was obtained by the slow cooling of a hot solution in ethyl acetate in a refrigerator.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. Numerical details are listed in Table 1. All H atoms on C were placed in idealized positions, guided by difference maps, with C—H bond distances of 0.95 Å. For (I), coordinates of the H atom on the N atom were refined, while for (II), this atom was placed by HFIX 43, with an N—H distance of 0.88 Å. Displacement parameters for all H atoms were assigned as U_iso(H) = 1.2U_eq(parent). The crystal of (I) was a slight nonmerohedral twin, by 180° rotation about the (001) reciprocal lattice direction. The twin law is -1.000 0.000 0.000/ 0.000 -1.000 0.000/ -0.226 -0.129 1.000. Refinement was versus HKLF 5 data, and the twin ratio refined to 0.9477 (8):0.0523 (8).

S3. Results and discussion

Both (I) (Fig. 1) and (II) (Fig. 2) crystallize with two independent molecules in the asymmetric unit and, for both, the two molecules are virtually identical. A least-squares overlay (CCDC, 2014) of the 11 non-H atoms in (I) yields an r.m.s. deviation of only 0.013 Å, and an overlay of the 12 non-H atoms in (II) gives an only slightly larger r.m.s. deviation of 0.054 Å. Both overlays are shown in Fig. 3. Cremer & Pople (1975) puckering parameters for the six-membered tellurocycle ring in (I) are (averages of two) Q = 0.786 (4), θ = 63.5 (3)° and φ = 325.5 (4)°, indicative of an approximate screw-boat conformation (Boeyens, 1978), the ideal form having θ = 67.5° and φ = 330°. For the seven-membered ring in (II), the Cremer–Pople puckering parameters are (average of two) q₂ = 1.176 (5) Å and q₃ = 0.244 (5) Å, phase angles φ₂ = 14.5 (3)° and φ₃ = 52.6 (11)°, and total puckering amplitude Q = 1.201 (4) Å.

The geometry of (I) about the Te atom is slightly different from that of its sulfur analog, with C—Te—C angles for the two unit-cell molecules of 85.89 (15) and 85.49 (15)°, as compared to a C—S—C angle of 98.25 (19)° for the sulfur analog (Rajnikant et al., 2004). This results in a geometry which places atoms C8 and C16 out of the plane defined by the N, Te and phenyl C atoms by 1.218 (3) and 1.220 (3) Å, respectively. When compared to (I), the C—Te—C angle reported for tetra­valent 1,1-di­chloro-1,1-di­hydro-2H-1,4-benzotellurazin-3(4H)-one was somewhat larger [91.53 (6)°; McMullen et al., 2013].

While for both (I) and (II), the N—H groups form inter­molecular N—H···O hydrogen bonds (Table 2 and 3), both the hydrogen-bonding patterns and the overall packing are quite different. Compound (I) forms a layered structure, with separate two-dimensional layers containing only Te1 molecules at z = 1/2 and only Te2 molecules at z = 1, both of which are illustrated in Fig. 4. In each layer, there are two distinct types of inter­molecular contacts, namely hydrogen bonds and Te···O contacts. In the Te1 layer, an R₂²(8) dimer (Etter, 1990) exists about the inversion center at (0, 0, 1/2). In addition, there are Te···O contacts to O atoms at (x+1, y, z) [3.200 (3) Å] and at (-x, -y+1, -z+1) [3.159 (3) Å], thus forming a centrosymmetric array of four molecules about (1/2, 1/2, 1/2). The Te1···Te1' distance [3.8234 (6) Å] across this center is also shorter than the sum of the van der Waals radii by 0.3 Å. The layer is nonplanar and propagates in the a and b directions by the inversion centers at z = 1/2. The layer containing Te2 at z = 1 is quite similar, as illustrated in Fig. 4. The R₂²(8) hydrogen-bonded dimer is about the inversion center at (1/2, 1/2, 1), and the centrosymmetric array of four molecules formed by the Te···O contacts is about (0, 0, 1), with Te2···O distances 3.173 (3) and 3.166 (3) Å, and a Te2···Te2' distance of 3.8226 (6)Å. The layer is propagated by the inversion centers at z = 1 and is thus parallel to the Te1 layer.

In (II), the packing is much simpler. The hydrogen-bonding pattern is C(4) chains in the [100] direction, with alternating Te1 and Te2 molecules, as shown in Fig. 5. There are no Te···O contacts and no Te···Te distances shorter than 4.415 Å.

Structure description

There is a paucity of data concerning the structures of six-membered tellurium- and nitro­gen-containing (Te—N) heterocycles. The few reported compounds comprise a small number of benzotellurazine derivatives (Detty & O'Regan, 1994). Of these, only 10H-phenotellurazine (Junk & Irgolic, 1989) and 1,1-di­chloro-1,1-di­hydro-2H-1,4-benzotellurazin-3(4H)-one (McMullen et al., 2013) were characterized by X-ray crystallography. Even fewer seven-membered Te—N heterocycles are known. The preparation of 2H-1,4-benzotellurazin-3(4H)-one, (I), was reported twice (Sadekov et al., 1993; McMullen et al., 2013), but no structural parameters were published. In addition, 11-(4-methyl­phenyl)­dibenzo[b,f][1,4]tellurazepine was prepared (Ladatko et al., 1987) but not structurally characterized. In contrast, benzo­thia­zinones and benzo­thia­zepines are well established, the latter being of importance as calcium-channel regulators (Mohacsi & O'Brien, 1991; Rampe & Tiggle, 1993).

We report here the structures of two tellurium-containing compounds, namely (I) and 2,3-di­hydro-1,5-benzotellurazepin-4(5H)-one, (II). Structural characterizations of the sulfur analogs of both (I) and (II) are reported in the literature (Rajnikant et al., 2004; Qin & Zhao, 2006).

The synthesis of (I) was reported previously (McMullen et al., 2013). Well-formed crystals were obtained by open air evaporation of a solution in di­chloro­methane.

A 25 ml Erlenmeyer flask was charged with bis­(2-amino­phenyl) ditelluride (250 mg, 0.57 mmol) prepared according to the published of McMullen et al. (2013), pyridine (90 mg, 1.14 mmol) and di­chloro­methane (4 ml). A solution of 3-bromo­propanoyl chloride (145 mg, 1.14 mmol) in di­chloro­methane (0.5 ml) was added with a pipette and the mixture set aside for 4 h. After this time, a precipitate of bis­[2-(3-chloro­propionamido)­phenyl] ditelluride had formed, which was collected by filtration and washed with methanol (1 ml). The damp crude solid was suspended in methanol (5 ml), placed in a 25 ml round-bottomed flask with magnetic stirring and a reflux condenser, heated to reflux, and sodium borohydride added through the condenser until the red color had faded (approximately 50 mg NaBH₄ consumed). Heating was discontinued, the flask content diluted with water (5 ml) and refrigerated for 1 h. The crude product was filtered and washed with cold methanol (approximately 1 ml). It was taken up in hot ethanol (8 ml), filtered hot though a cotton plug and placed in a freezer to crystallize. Recrystallization from ethanol furnished off-white crystals (yield 87 mg, 27.8%; m.p. 494–495 K). ¹H NMR (CDCl₃): δ 2.74 (triplet, 2H), 3.48 (triplet, 2H), 7.03 (triplet, 1H), 7.12 (doublet, 1H), 7.36 (triplet, 1H), 7.89 (triplet, 1H), 8.12 (broad singlet, 1H). ¹³C NMR (CDCl₃): δ 2.80, 34.39, 109.84, 123.86, 127.14, 130.44, 140.91, 143.06, 174.69. The compound oxidizes slowly in solution. A sample suitable for X-ray crystallography was obtained by the slow cooling of a hot solution in ethyl acetate in a refrigerator.

Both (I) (Fig. 1) and (II) (Fig. 2) crystallize with two independent molecules in the asymmetric unit and, for both, the two molecules are virtually identical. A least-squares overlay (CCDC, 2014) of the 11 non-H atoms in (I) yields an r.m.s. deviation of only 0.013 Å, and an overlay of the 12 non-H atoms in (II) gives an only slightly larger r.m.s. deviation of 0.054 Å. Both overlays are shown in Fig. 3. Cremer & Pople (1975) puckering parameters for the six-membered tellurocycle ring in (I) are (averages of two) Q = 0.786 (4), θ = 63.5 (3)° and φ = 325.5 (4)°, indicative of an approximate screw-boat conformation (Boeyens, 1978), the ideal form having θ = 67.5° and φ = 330°. For the seven-membered ring in (II), the Cremer–Pople puckering parameters are (average of two) q₂ = 1.176 (5) Å and q₃ = 0.244 (5) Å, phase angles φ₂ = 14.5 (3)° and φ₃ = 52.6 (11)°, and total puckering amplitude Q = 1.201 (4) Å.

The geometry of (I) about the Te atom is slightly different from that of its sulfur analog, with C—Te—C angles for the two unit-cell molecules of 85.89 (15) and 85.49 (15)°, as compared to a C—S—C angle of 98.25 (19)° for the sulfur analog (Rajnikant et al., 2004). This results in a geometry which places atoms C8 and C16 out of the plane defined by the N, Te and phenyl C atoms by 1.218 (3) and 1.220 (3) Å, respectively. When compared to (I), the C—Te—C angle reported for tetra­valent 1,1-di­chloro-1,1-di­hydro-2H-1,4-benzotellurazin-3(4H)-one was somewhat larger [91.53 (6)°; McMullen et al., 2013].

While for both (I) and (II), the N—H groups form inter­molecular N—H···O hydrogen bonds (Table 2 and 3), both the hydrogen-bonding patterns and the overall packing are quite different. Compound (I) forms a layered structure, with separate two-dimensional layers containing only Te1 molecules at z = 1/2 and only Te2 molecules at z = 1, both of which are illustrated in Fig. 4. In each layer, there are two distinct types of inter­molecular contacts, namely hydrogen bonds and Te···O contacts. In the Te1 layer, an R₂²(8) dimer (Etter, 1990) exists about the inversion center at (0, 0, 1/2). In addition, there are Te···O contacts to O atoms at (x+1, y, z) [3.200 (3) Å] and at (-x, -y+1, -z+1) [3.159 (3) Å], thus forming a centrosymmetric array of four molecules about (1/2, 1/2, 1/2). The Te1···Te1' distance [3.8234 (6) Å] across this center is also shorter than the sum of the van der Waals radii by 0.3 Å. The layer is nonplanar and propagates in the a and b directions by the inversion centers at z = 1/2. The layer containing Te2 at z = 1 is quite similar, as illustrated in Fig. 4. The R₂²(8) hydrogen-bonded dimer is about the inversion center at (1/2, 1/2, 1), and the centrosymmetric array of four molecules formed by the Te···O contacts is about (0, 0, 1), with Te2···O distances 3.173 (3) and 3.166 (3) Å, and a Te2···Te2' distance of 3.8226 (6)Å. The layer is propagated by the inversion centers at z = 1 and is thus parallel to the Te1 layer.

In (II), the packing is much simpler. The hydrogen-bonding pattern is C(4) chains in the [100] direction, with alternating Te1 and Te2 molecules, as shown in Fig. 5. There are no Te···O contacts and no Te···Te distances shorter than 4.415 Å.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 1. Numerical details are listed in Table 1. All H atoms on C were placed in idealized positions, guided by difference maps, with C—H bond distances of 0.95 Å. For (I), coordinates of the H atom on the N atom were refined, while for (II), this atom was placed by HFIX 43, with an N—H distance of 0.88 Å. Displacement parameters for all H atoms were assigned as U_iso(H) = 1.2U_eq(parent). The crystal of (I) was a slight nonmerohedral twin, by 180° rotation about the (001) reciprocal lattice direction. The twin law is -1.000 0.000 0.000/ 0.000 -1.000 0.000/ -0.226 -0.129 1.000. Refinement was versus HKLF 5 data, and the twin ratio refined to 0.9477 (8):0.0523 (8).

Computing details

Data collection: COLLECT (Nonius, 2000) for Junk58; APEX2 (Bruker, 2009) for Junk60. Cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for Junk58; SAINT (Bruker, 2009) for Junk60. Data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997) for Junk58; SAINT (Bruker, 2009) for Junk60. Program(s) used to solve structure: SIR97 (Altomare et al., 1999) for Junk58; SHELXS97 (Sheldrick, 2008) for Junk60. For both compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures

	Fig. 1. A view of the two independent molecules of (I), shown with 50% probability displacement ellipsoids.
	Fig. 2. A view of the two independent molecules of (II), shown with 50% probability displacement ellipsoids.
	Fig. 3. Overlays of the two independent molecules in (I) (left) and in (II) (right).
	Fig. 4. Views of the Te1 and Te2 layers in (I), illustrating the hydrogen-bonded dimers and close contacts. All H atoms, except those on N atoms, have been omitted. Generic atoms labels without symmetry codes have been used.
	Fig. 5. The unit cell of (II), showing the hydrogen-bonded chains. All H atoms, except those on N atoms, have been omitted. Generic atoms labels without symmetry codes have been used.

(Junk58) 2H-1,4-Benzotellurazin-3(4H)-one

Crystal data

C8H7NOTe	Z = 4
Mr = 260.75	F(000) = 488
Triclinic, P1	Dx = 2.130 Mg m^−3
a = 6.5667 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.892 (1) Å	Cell parameters from 4598 reflections
c = 17.2051 (15) Å	θ = 2.5–30.5°
α = 87.291 (9)°	µ = 3.60 mm^−1
β = 86.833 (5)°	T = 180 K
γ = 65.990 (6)°	Fragment, yellow
V = 812.95 (17) Å^3	0.17 × 0.12 × 0.05 mm

Data collection

Nonius KappaCCD diffractometer	7392 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
ω and φ scans	θmax = 30.5°, θmin = 2.8°
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.580, Tmax = 0.841	k = −11→11
8596 measured reflections	l = −24→24
8596 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0142P)^2 + 2.9489P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.077	(Δ/σ)max = 0.001
S = 1.19	Δρmax = 0.78 e Å^−3
8596 reflections	Δρmin = −0.92 e Å^−3
207 parameters	Extinction correction: SHELXL2014 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0070 (4)

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. The crystal was a slight non-merohedral twin, by 180.0 degree rotation about 0. 0. 1. reciprocal lattice direction Twin law: [ -1.000 0.000 0.000] [ 0.000 -1.000 0.000] [ -0.226 -0.129 1.000] Refinement used an HKLF 5 file, and BASF refined to 0.0523 (8).

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

	x	y	z	Uiso*/Ueq
Te1	0.40529 (4)	0.36605 (4)	0.43087 (2)	0.02236 (9)
O1	−0.1066 (5)	0.2475 (4)	0.49546 (19)	0.0283 (7)
N1	0.2007 (6)	0.0508 (5)	0.4307 (2)	0.0234 (7)
H1N	0.170 (8)	−0.045 (7)	0.454 (3)	0.028*
C1	0.5281 (7)	0.1051 (6)	0.3785 (2)	0.0204 (8)
C2	0.7311 (7)	0.0366 (7)	0.3358 (3)	0.0290 (9)
H2	0.8173	0.1086	0.3307	0.035*
C3	0.8095 (8)	−0.1338 (7)	0.3009 (3)	0.0330 (10)
H3	0.9507	−0.1804	0.2739	0.040*
C4	0.6792 (8)	−0.2366 (6)	0.3058 (3)	0.0302 (10)
H4	0.7296	−0.3519	0.2806	0.036*
C5	0.4762 (8)	−0.1707 (6)	0.3473 (2)	0.0261 (9)
H5	0.3881	−0.2413	0.3507	0.031*
C6	0.4009 (7)	−0.0008 (6)	0.3843 (2)	0.0207 (8)
C7	0.0514 (7)	0.2243 (6)	0.4479 (2)	0.0209 (8)
C8	0.0801 (6)	0.3843 (6)	0.4061 (2)	0.0207 (8)
H8A	−0.0362	0.5032	0.4243	0.025*
H8B	0.0675	0.3779	0.3493	0.025*
Te2	0.10753 (4)	0.14841 (4)	0.93304 (2)	0.02181 (8)
O2	0.6095 (5)	0.2517 (4)	0.99498 (19)	0.0272 (7)
N2	0.3192 (6)	0.4592 (5)	0.9293 (2)	0.0230 (7)
H2N	0.348 (8)	0.550 (7)	0.952 (3)	0.028*
C9	−0.0003 (6)	0.4149 (6)	0.8795 (2)	0.0199 (8)
C10	−0.1962 (7)	0.4915 (7)	0.8380 (2)	0.0278 (9)
H10	−0.2850	0.4228	0.8343	0.033*
C11	−0.2630 (8)	0.6654 (7)	0.8022 (3)	0.0343 (11)
H11	−0.3995	0.7174	0.7760	0.041*
C12	−0.1298 (8)	0.7634 (7)	0.8048 (3)	0.0306 (10)
H12	−0.1728	0.8809	0.7787	0.037*
C13	0.0656 (8)	0.6909 (6)	0.8452 (3)	0.0273 (9)
H13	0.1560	0.7588	0.8471	0.033*
C14	0.1292 (7)	0.5174 (6)	0.8833 (2)	0.0198 (8)
C15	0.4612 (6)	0.2831 (6)	0.9473 (2)	0.0201 (8)
C16	0.4388 (6)	0.1299 (6)	0.9057 (2)	0.0204 (8)
H16A	0.5509	0.0081	0.9234	0.025*
H16B	0.4614	0.1442	0.8488	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Te1	0.02183 (14)	0.02075 (16)	0.02670 (15)	−0.01071 (11)	−0.00028 (10)	−0.00319 (11)
O1	0.0228 (15)	0.0230 (17)	0.0381 (18)	−0.0089 (13)	0.0050 (13)	−0.0028 (13)
N1	0.0233 (17)	0.0160 (18)	0.0302 (19)	−0.0080 (15)	0.0023 (14)	0.0015 (14)
C1	0.0194 (18)	0.020 (2)	0.0195 (18)	−0.0050 (16)	−0.0038 (14)	0.0009 (15)
C2	0.024 (2)	0.036 (3)	0.024 (2)	−0.0085 (19)	0.0006 (16)	−0.0042 (18)
C3	0.027 (2)	0.035 (3)	0.026 (2)	−0.001 (2)	0.0027 (17)	−0.0066 (19)
C4	0.036 (2)	0.021 (2)	0.021 (2)	0.0017 (19)	−0.0025 (17)	−0.0024 (17)
C5	0.034 (2)	0.017 (2)	0.024 (2)	−0.0064 (18)	−0.0036 (17)	0.0002 (16)
C6	0.0239 (19)	0.016 (2)	0.0192 (18)	−0.0050 (16)	−0.0027 (15)	0.0017 (15)
C7	0.0186 (18)	0.019 (2)	0.026 (2)	−0.0078 (16)	−0.0048 (15)	−0.0015 (16)
C8	0.0188 (18)	0.017 (2)	0.0236 (19)	−0.0050 (15)	−0.0025 (14)	0.0001 (15)
Te2	0.02169 (14)	0.02145 (16)	0.02455 (15)	−0.01097 (12)	−0.00357 (10)	0.00162 (11)
O2	0.0223 (14)	0.0217 (16)	0.0369 (17)	−0.0071 (13)	−0.0108 (12)	−0.0001 (13)
N2	0.0243 (17)	0.0159 (18)	0.0293 (18)	−0.0078 (14)	−0.0076 (14)	−0.0014 (14)
C9	0.0188 (18)	0.020 (2)	0.0178 (17)	−0.0053 (16)	−0.0005 (14)	−0.0001 (15)
C10	0.023 (2)	0.035 (3)	0.023 (2)	−0.0085 (19)	−0.0028 (16)	0.0023 (18)
C11	0.024 (2)	0.039 (3)	0.024 (2)	0.002 (2)	−0.0032 (17)	0.005 (2)
C12	0.037 (2)	0.022 (2)	0.022 (2)	−0.0006 (19)	−0.0008 (18)	0.0033 (17)
C13	0.034 (2)	0.020 (2)	0.026 (2)	−0.0082 (18)	−0.0005 (17)	−0.0008 (17)
C14	0.0206 (18)	0.015 (2)	0.0199 (18)	−0.0028 (15)	−0.0026 (14)	−0.0019 (15)
C15	0.0159 (17)	0.020 (2)	0.0251 (19)	−0.0082 (16)	0.0003 (14)	0.0008 (16)
C16	0.0193 (18)	0.017 (2)	0.0236 (19)	−0.0057 (15)	−0.0010 (14)	−0.0011 (15)

Geometric parameters (Å, º)

Te1—C1	2.109 (4)	Te2—C9	2.110 (4)
Te1—C8	2.147 (4)	Te2—C16	2.147 (4)
O1—C7	1.243 (5)	O2—C15	1.248 (5)
N1—C7	1.356 (5)	N2—C15	1.354 (6)
N1—C6	1.418 (5)	N2—C14	1.415 (5)
N1—H1N	0.93 (5)	N2—H2N	0.92 (5)
C1—C2	1.397 (6)	C9—C14	1.397 (6)
C1—C6	1.399 (6)	C9—C10	1.399 (6)
C2—C3	1.383 (7)	C10—C11	1.384 (7)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.396 (7)	C11—C12	1.387 (8)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.387 (6)	C12—C13	1.386 (7)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.398 (6)	C13—C14	1.400 (6)
C5—H5	0.9500	C13—H13	0.9500
C7—C8	1.497 (6)	C15—C16	1.494 (6)
C8—H8A	0.9900	C16—H16A	0.9900
C8—H8B	0.9900	C16—H16B	0.9900
C1—Te1—C8	85.89 (15)	C9—Te2—C16	85.49 (15)
C7—N1—C6	127.9 (4)	C15—N2—C14	127.6 (4)
C7—N1—H1N	116 (3)	C15—N2—H2N	115 (3)
C6—N1—H1N	116 (3)	C14—N2—H2N	117 (3)
C2—C1—C6	118.7 (4)	C14—C9—C10	118.4 (4)
C2—C1—Te1	121.8 (3)	C14—C9—Te2	119.6 (3)
C6—C1—Te1	119.5 (3)	C10—C9—Te2	121.9 (3)
C3—C2—C1	121.5 (4)	C11—C10—C9	121.2 (4)
C3—C2—H2	119.3	C11—C10—H10	119.4
C1—C2—H2	119.3	C9—C10—H10	119.4
C2—C3—C4	119.4 (4)	C10—C11—C12	119.7 (4)
C2—C3—H3	120.3	C10—C11—H11	120.2
C4—C3—H3	120.3	C12—C11—H11	120.2
C5—C4—C3	120.2 (4)	C13—C12—C11	120.4 (4)
C5—C4—H4	119.9	C13—C12—H12	119.8
C3—C4—H4	119.9	C11—C12—H12	119.8
C4—C5—C6	120.1 (4)	C12—C13—C14	119.7 (4)
C4—C5—H5	119.9	C12—C13—H13	120.1
C6—C5—H5	119.9	C14—C13—H13	120.1
C5—C6—C1	120.2 (4)	C9—C14—C13	120.5 (4)
C5—C6—N1	117.0 (4)	C9—C14—N2	122.6 (4)
C1—C6—N1	122.7 (4)	C13—C14—N2	116.8 (4)
O1—C7—N1	120.4 (4)	O2—C15—N2	120.7 (4)
O1—C7—C8	121.8 (4)	O2—C15—C16	121.7 (4)
N1—C7—C8	117.8 (4)	N2—C15—C16	117.6 (4)
C7—C8—Te1	107.2 (3)	C15—C16—Te2	106.7 (3)
C7—C8—H8A	110.3	C15—C16—H16A	110.4
Te1—C8—H8A	110.3	Te2—C16—H16A	110.4
C7—C8—H8B	110.3	C15—C16—H16B	110.4
Te1—C8—H8B	110.3	Te2—C16—H16B	110.4
H8A—C8—H8B	108.5	H16A—C16—H16B	108.6
C6—C1—C2—C3	−1.2 (6)	C14—C9—C10—C11	−0.8 (6)
Te1—C1—C2—C3	−179.3 (3)	Te2—C9—C10—C11	−179.1 (3)
C1—C2—C3—C4	2.5 (7)	C9—C10—C11—C12	2.5 (7)
C2—C3—C4—C5	−2.0 (7)	C10—C11—C12—C13	−2.2 (7)
C3—C4—C5—C6	0.2 (7)	C11—C12—C13—C14	0.3 (7)
C4—C5—C6—C1	1.1 (6)	C10—C9—C14—C13	−1.1 (6)
C4—C5—C6—N1	−175.2 (4)	Te2—C9—C14—C13	177.2 (3)
C2—C1—C6—C5	−0.6 (6)	C10—C9—C14—N2	174.4 (4)
Te1—C1—C6—C5	177.5 (3)	Te2—C9—C14—N2	−7.4 (5)
C2—C1—C6—N1	175.4 (4)	C12—C13—C14—C9	1.4 (6)
Te1—C1—C6—N1	−6.4 (5)	C12—C13—C14—N2	−174.4 (4)
C7—N1—C6—C5	−153.1 (4)	C15—N2—C14—C9	31.2 (6)
C7—N1—C6—C1	30.8 (6)	C15—N2—C14—C13	−153.2 (4)
C6—N1—C7—O1	−173.3 (4)	C14—N2—C15—O2	−172.7 (4)
C6—N1—C7—C8	8.5 (6)	C14—N2—C15—C16	9.5 (6)
O1—C7—C8—Te1	123.3 (4)	O2—C15—C16—Te2	122.1 (4)
N1—C7—C8—Te1	−58.6 (4)	N2—C15—C16—Te2	−60.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.93 (5)	1.96 (5)	2.890 (5)	179 (5)
N2—H2N···O2^ii	0.92 (5)	1.97 (5)	2.888 (5)	176 (5)

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

(Junk60) 2,3-Dihydro-1,5-benzotellurazepin-4(5H)-one

Crystal data

C9H9NOTe	F(000) = 1040
Mr = 274.77	Dx = 2.008 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 7.7404 (3) Å	Cell parameters from 4220 reflections
b = 9.6523 (5) Å	θ = 3.6–68.7°
c = 24.4699 (10) Å	µ = 25.43 mm^−1
β = 96.000 (2)°	T = 90 K
V = 1818.20 (14) Å^3	Lath, yellow
Z = 8	0.27 × 0.08 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer	2723 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
φ and ω scans	θmax = 69.3°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −7→9
Tmin = 0.055, Tmax = 0.516	k = −11→11
15400 measured reflections	l = −29→28
3304 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)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 3.7101P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
3304 reflections	Δρmax = 1.53 e Å^−3
217 parameters	Δρmin = −1.28 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	0.72004 (4)	0.27797 (4)	0.33076 (2)	0.02505 (12)
O1	0.7783 (5)	0.2118 (4)	0.50188 (15)	0.0289 (9)
N1	0.9572 (5)	0.1379 (5)	0.44165 (17)	0.0212 (9)
H1N	1.0444	0.1670	0.4647	0.025*
C1	0.9142 (6)	0.1218 (5)	0.3405 (2)	0.0184 (10)
C2	1.0006 (7)	0.0832 (5)	0.3911 (2)	0.0198 (11)
C3	0.7973 (6)	0.1504 (5)	0.45835 (19)	0.0190 (10)
C4	0.6445 (6)	0.0872 (6)	0.4246 (2)	0.0228 (11)
H4A	0.5634	0.0481	0.4493	0.027*
H4B	0.6846	0.0107	0.4022	0.027*
C5	0.5502 (7)	0.1948 (6)	0.3871 (2)	0.0250 (11)
H5A	0.5088	0.2708	0.4096	0.030*
H5B	0.4477	0.1517	0.3662	0.030*
C6	0.9696 (7)	0.0683 (7)	0.2924 (2)	0.0316 (13)
H6	0.9094	0.0921	0.2579	0.038*
C7	1.1112 (8)	−0.0190 (7)	0.2946 (3)	0.0418 (17)
H7	1.1494	−0.0536	0.2615	0.050*
C8	1.1977 (8)	−0.0563 (7)	0.3447 (3)	0.0368 (15)
H8	1.2946	−0.1170	0.3462	0.044*
C9	1.1427 (7)	−0.0048 (6)	0.3931 (3)	0.0298 (13)
H9	1.2026	−0.0300	0.4275	0.036*
Te2	0.34547 (5)	0.26825 (4)	0.68056 (2)	0.02658 (12)
O2	0.2778 (5)	0.1949 (4)	0.50500 (15)	0.0284 (8)
N2	0.4948 (6)	0.3008 (4)	0.55636 (17)	0.0213 (9)
H2N	0.5667	0.2472	0.5405	0.026*
C10	0.5278 (7)	0.4031 (5)	0.6497 (2)	0.0222 (11)
C11	0.5732 (7)	0.3955 (5)	0.5957 (2)	0.0218 (11)
C12	0.3248 (7)	0.2822 (6)	0.5401 (2)	0.0231 (11)
C13	0.1945 (7)	0.3723 (6)	0.5657 (2)	0.0311 (13)
H13A	0.0914	0.3870	0.5388	0.037*
H13B	0.2471	0.4639	0.5750	0.037*
C14	0.1370 (8)	0.3042 (7)	0.6184 (3)	0.0367 (14)
H14A	0.0795	0.2148	0.6083	0.044*
H14B	0.0504	0.3649	0.6335	0.044*
C15	0.6161 (7)	0.4966 (6)	0.6863 (2)	0.0269 (12)
H15	0.5839	0.5048	0.7226	0.032*
C16	0.7512 (7)	0.5779 (6)	0.6702 (2)	0.0317 (13)
H16	0.8124	0.6394	0.6957	0.038*
C17	0.7952 (7)	0.5685 (6)	0.6173 (2)	0.0307 (13)
H17	0.8864	0.6242	0.6061	0.037*
C18	0.7069 (7)	0.4780 (5)	0.5803 (2)	0.0259 (12)
H18	0.7382	0.4724	0.5438	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Te1	0.0217 (2)	0.0317 (2)	0.02171 (19)	0.00184 (13)	0.00232 (13)	0.00916 (13)
O1	0.030 (2)	0.037 (2)	0.0203 (18)	0.0028 (17)	0.0071 (16)	−0.0070 (16)
N1	0.019 (2)	0.027 (2)	0.018 (2)	0.0036 (18)	0.0019 (17)	−0.0012 (17)
C1	0.017 (3)	0.021 (3)	0.017 (2)	−0.005 (2)	0.004 (2)	−0.0038 (19)
C2	0.020 (3)	0.018 (3)	0.022 (2)	0.000 (2)	0.006 (2)	−0.0017 (19)
C3	0.024 (3)	0.019 (3)	0.015 (2)	0.008 (2)	0.005 (2)	0.0038 (19)
C4	0.019 (3)	0.028 (3)	0.023 (3)	0.000 (2)	0.007 (2)	0.003 (2)
C5	0.017 (3)	0.035 (3)	0.024 (3)	−0.002 (2)	0.004 (2)	0.004 (2)
C6	0.030 (3)	0.042 (4)	0.023 (3)	−0.010 (3)	0.005 (2)	−0.010 (2)
C7	0.040 (4)	0.051 (4)	0.038 (4)	−0.007 (3)	0.021 (3)	−0.026 (3)
C8	0.032 (3)	0.031 (3)	0.050 (4)	0.006 (3)	0.019 (3)	−0.011 (3)
C9	0.020 (3)	0.035 (3)	0.036 (3)	0.005 (2)	0.008 (2)	0.004 (2)
Te2	0.0330 (2)	0.0267 (2)	0.02189 (19)	0.00434 (14)	0.01152 (15)	0.00238 (13)
O2	0.025 (2)	0.034 (2)	0.0253 (19)	−0.0007 (17)	−0.0027 (16)	−0.0047 (17)
N2	0.022 (2)	0.023 (2)	0.019 (2)	0.0037 (18)	0.0062 (17)	−0.0030 (17)
C10	0.019 (3)	0.025 (3)	0.022 (3)	0.003 (2)	0.001 (2)	0.002 (2)
C11	0.025 (3)	0.017 (3)	0.023 (3)	0.005 (2)	−0.002 (2)	0.001 (2)
C12	0.024 (3)	0.028 (3)	0.017 (2)	0.007 (2)	−0.001 (2)	0.001 (2)
C13	0.023 (3)	0.033 (3)	0.037 (3)	0.005 (2)	0.002 (2)	0.002 (3)
C14	0.037 (4)	0.036 (3)	0.037 (3)	0.003 (3)	0.004 (3)	−0.001 (3)
C15	0.027 (3)	0.027 (3)	0.025 (3)	0.012 (2)	−0.004 (2)	−0.005 (2)
C16	0.029 (3)	0.026 (3)	0.037 (3)	0.002 (2)	−0.012 (3)	−0.005 (2)
C17	0.026 (3)	0.023 (3)	0.043 (3)	0.004 (2)	−0.001 (3)	0.004 (2)
C18	0.027 (3)	0.024 (3)	0.028 (3)	0.003 (2)	0.007 (2)	0.001 (2)

Geometric parameters (Å, º)

Te1—C1	2.124 (5)	Te2—C10	2.117 (5)
Te1—C5	2.158 (5)	Te2—C14	2.127 (6)
O1—C3	1.241 (6)	O2—C12	1.232 (7)
N1—C3	1.348 (6)	N2—C12	1.347 (7)
N1—C2	1.417 (6)	N2—C11	1.417 (7)
N1—H1N	0.8800	N2—H2N	0.8800
C1—C6	1.393 (7)	C10—C15	1.399 (8)
C1—C2	1.396 (7)	C10—C11	1.404 (7)
C2—C9	1.386 (8)	C11—C18	1.389 (7)
C3—C4	1.500 (7)	C12—C13	1.515 (7)
C4—C5	1.520 (7)	C13—C14	1.554 (8)
C4—H4A	0.9900	C13—H13A	0.9900
C4—H4B	0.9900	C13—H13B	0.9900
C5—H5A	0.9900	C14—H14A	0.9900
C5—H5B	0.9900	C14—H14B	0.9900
C6—C7	1.379 (9)	C15—C16	1.397 (8)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.383 (10)	C16—C17	1.377 (8)
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.390 (8)	C17—C18	1.386 (8)
C8—H8	0.9500	C17—H17	0.9500
C9—H9	0.9500	C18—H18	0.9500
C1—Te1—C5	97.77 (19)	C10—Te2—C14	97.4 (2)
C3—N1—C2	127.4 (4)	C12—N2—C11	128.5 (4)
C3—N1—H1N	116.3	C12—N2—H2N	115.8
C2—N1—H1N	116.3	C11—N2—H2N	115.8
C6—C1—C2	119.3 (5)	C15—C10—C11	118.9 (5)
C6—C1—Te1	116.4 (4)	C15—C10—Te2	117.9 (4)
C2—C1—Te1	123.8 (4)	C11—C10—Te2	123.1 (4)
C9—C2—C1	119.9 (5)	C18—C11—C10	119.5 (5)
C9—C2—N1	117.3 (5)	C18—C11—N2	117.6 (5)
C1—C2—N1	122.7 (4)	C10—C11—N2	122.8 (5)
O1—C3—N1	119.9 (5)	O2—C12—N2	120.4 (5)
O1—C3—C4	120.6 (4)	O2—C12—C13	121.3 (5)
N1—C3—C4	119.5 (4)	N2—C12—C13	118.3 (5)
C3—C4—C5	110.8 (4)	C12—C13—C14	111.1 (5)
C3—C4—H4A	109.5	C12—C13—H13A	109.4
C5—C4—H4A	109.5	C14—C13—H13A	109.4
C3—C4—H4B	109.5	C12—C13—H13B	109.4
C5—C4—H4B	109.5	C14—C13—H13B	109.4
H4A—C4—H4B	108.1	H13A—C13—H13B	108.0
C4—C5—Te1	110.7 (3)	C13—C14—Te2	113.7 (4)
C4—C5—H5A	109.5	C13—C14—H14A	108.8
Te1—C5—H5A	109.5	Te2—C14—H14A	108.8
C4—C5—H5B	109.5	C13—C14—H14B	108.8
Te1—C5—H5B	109.5	Te2—C14—H14B	108.8
H5A—C5—H5B	108.1	H14A—C14—H14B	107.7
C7—C6—C1	120.5 (6)	C16—C15—C10	120.8 (5)
C7—C6—H6	119.7	C16—C15—H15	119.6
C1—C6—H6	119.7	C10—C15—H15	119.6
C6—C7—C8	120.1 (5)	C17—C16—C15	119.6 (5)
C6—C7—H7	119.9	C17—C16—H16	120.2
C8—C7—H7	119.9	C15—C16—H16	120.2
C7—C8—C9	120.0 (6)	C16—C17—C18	120.2 (5)
C7—C8—H8	120.0	C16—C17—H17	119.9
C9—C8—H8	120.0	C18—C17—H17	119.9
C2—C9—C8	120.2 (6)	C17—C18—C11	121.0 (5)
C2—C9—H9	119.9	C17—C18—H18	119.5
C8—C9—H9	119.9	C11—C18—H18	119.5
C6—C1—C2—C9	1.6 (8)	C15—C10—C11—C18	1.5 (8)
Te1—C1—C2—C9	−170.5 (4)	Te2—C10—C11—C18	−173.3 (4)
C6—C1—C2—N1	177.1 (5)	C15—C10—C11—N2	177.8 (5)
Te1—C1—C2—N1	5.0 (7)	Te2—C10—C11—N2	3.0 (7)
C3—N1—C2—C9	−136.9 (5)	C12—N2—C11—C18	−129.5 (6)
C3—N1—C2—C1	47.4 (7)	C12—N2—C11—C10	54.2 (8)
C2—N1—C3—O1	−173.6 (5)	C11—N2—C12—O2	179.8 (5)
C2—N1—C3—C4	7.6 (7)	C11—N2—C12—C13	0.5 (8)
O1—C3—C4—C5	84.2 (6)	O2—C12—C13—C14	91.0 (6)
N1—C3—C4—C5	−97.1 (5)	N2—C12—C13—C14	−89.8 (6)
C3—C4—C5—Te1	61.0 (5)	C12—C13—C14—Te2	59.7 (6)
C2—C1—C6—C7	−1.7 (8)	C11—C10—C15—C16	−2.1 (8)
Te1—C1—C6—C7	171.0 (5)	Te2—C10—C15—C16	173.0 (4)
C1—C6—C7—C8	1.2 (9)	C10—C15—C16—C17	1.6 (8)
C6—C7—C8—C9	−0.5 (10)	C15—C16—C17—C18	−0.5 (8)
C1—C2—C9—C8	−0.9 (8)	C16—C17—C18—C11	0.0 (8)
N1—C2—C9—C8	−176.7 (5)	C10—C11—C18—C17	−0.5 (8)
C7—C8—C9—C2	0.4 (9)	N2—C11—C18—C17	−177.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2^i	0.88	1.98	2.839 (6)	164
N2—H2N···O1	0.88	2.00	2.818 (5)	153

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