Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615022378/sk3604sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615022378/sk3604Junk58sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615022378/sk3604Junk60sup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615022378/sk3604Junk58sup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615022378/sk3604Junk60sup5.cml |
CCDC references: 1438399; 1438398
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.
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 Uiso(H) = 1.2Ueq(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).
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.
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.
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 Uiso(H) = 1.2Ueq(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).
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).
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) Å3 | 0.17 × 0.12 × 0.05 mm |
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 on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0142P)2 + 2.9489P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0070 (4) |
C8H7NOTe | γ = 65.990 (6)° |
Mr = 260.75 | V = 812.95 (17) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.5667 (9) Å | Mo Kα radiation |
b = 7.892 (1) Å | µ = 3.60 mm−1 |
c = 17.2051 (15) Å | T = 180 K |
α = 87.291 (9)° | 0.17 × 0.12 × 0.05 mm |
β = 86.833 (5)° |
Nonius KappaCCD diffractometer | 8596 independent reflections |
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | 7392 reflections with I > 2σ(I) |
Tmin = 0.580, Tmax = 0.841 | Rint = 0.021 |
8596 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.19 | Δρmax = 0.78 e Å−3 |
8596 reflections | Δρmin = −0.92 e Å−3 |
207 parameters |
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). |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.93 (5) | 1.96 (5) | 2.890 (5) | 179 (5) |
N2—H2N···O2ii | 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. |
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) Å3 | Lath, yellow |
Z = 8 | 0.27 × 0.08 × 0.03 mm |
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 on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.039P)2 + 3.7101P] where P = (Fo2 + 2Fc2)/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 |
C9H9NOTe | V = 1818.20 (14) Å3 |
Mr = 274.77 | Z = 8 |
Monoclinic, P21/c | Cu Kα radiation |
a = 7.7404 (3) Å | µ = 25.43 mm−1 |
b = 9.6523 (5) Å | T = 90 K |
c = 24.4699 (10) Å | 0.27 × 0.08 × 0.03 mm |
β = 96.000 (2)° |
Bruker APEXII CCD diffractometer | 3304 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2723 reflections with I > 2σ(I) |
Tmin = 0.055, Tmax = 0.516 | Rint = 0.058 |
15400 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.06 | Δρmax = 1.53 e Å−3 |
3304 reflections | Δρmin = −1.28 e Å−3 |
217 parameters |
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. |
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 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. |
Experimental details
(Junk58) | (Junk60) | |
Crystal data | ||
Chemical formula | C8H7NOTe | C9H9NOTe |
Mr | 260.75 | 274.77 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 180 | 90 |
a, b, c (Å) | 6.5667 (9), 7.892 (1), 17.2051 (15) | 7.7404 (3), 9.6523 (5), 24.4699 (10) |
α, β, γ (°) | 87.291 (9), 86.833 (5), 65.990 (6) | 90, 96.000 (2), 90 |
V (Å3) | 812.95 (17) | 1818.20 (14) |
Z | 4 | 8 |
Radiation type | Mo Kα | Cu Kα |
µ (mm−1) | 3.60 | 25.43 |
Crystal size (mm) | 0.17 × 0.12 × 0.05 | 0.27 × 0.08 × 0.03 |
Data collection | ||
Diffractometer | Nonius KappaCCD | Bruker APEXII CCD |
Absorption correction | Multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.580, 0.841 | 0.055, 0.516 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8596, 8596, 7392 | 15400, 3304, 2723 |
Rint | 0.021 | 0.058 |
(sin θ/λ)max (Å−1) | 0.715 | 0.607 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.077, 1.19 | 0.035, 0.089, 1.06 |
No. of reflections | 8596 | 3304 |
No. of parameters | 207 | 217 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.78, −0.92 | 1.53, −1.28 |
Computer programs: COLLECT (Nonius, 2000), APEX2 (Bruker, 2009), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SAINT (Bruker, 2009), SIR97 (Altomare et al., 1999), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.93 (5) | 1.96 (5) | 2.890 (5) | 179 (5) |
N2—H2N···O2ii | 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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.88 | 1.98 | 2.839 (6) | 163.7 |
N2—H2N···O1 | 0.88 | 2.00 | 2.818 (5) | 153.4 |
Symmetry code: (i) x+1, y, z. |