Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047253/bt2520sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047253/bt2520Isup2.hkl |
CCDC reference: 664218
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.022
- wR factor = 0.053
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact Te1 .. F2 .. 2.89 Ang.
Author Response: The contact is a secondary intermolecular Te...F contact below the sum of the Te--F van der Waals radii as present in many tellurium--fluorine compounds |
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C19 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C20
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The tellurium(IV) difluoride (2-Me2NCH2C6H4)2TeF2 was prepared according to literature (Hammerl et al., 2007). A solution in chloroform stored for a period of 3 months in a glass vessel at 4°C results in the formation of colorless crystals of the title compound suitable for X-ray diffraction studies. The presence of Si in the structure results from the slow reaction of the tellurium(IV) difluoride with glass.
H atoms were refined with fixed individual displacement parameters [U(H) = 1.2Ueq(C) or U(H) = 1.5Ueq(Cmethyl)] using a riding model with C—H ranging from 0.95 Å, to 1.00 Å. The H atom bonded to O was freely refined.
As part of our recent studies regarding tellurium(II) and tellurium(IV) compounds with the intramolecular donor stabilizing substituent 2-Me2NCH2C6H4 (Hammerl et al., 2007) we obtained the title compound as a decomposition product.
In the title compound two intramolecular interactions between the aminomethyl nitrogen atom and the tellurium atom create two five-membered heterocycles with a 4-coordinated amine moiety (Te1···N1 2.719 (3) and Te1···N2 2.557 (2) Å). The Te1–O1 distance is with 1.9612 (17) Å slightly elongated compared to the calculated bond distance in [Ph2TeOH]+ (1.937 Å, Beckmann et al., 2005). The present hydrogen bridge O1–H1···F1 links the cation with the anion and exhibits a donor acceptor distance of 2.696 (2) Å. The tellurium atom is further coordinated by an intermolecular tellurium–fluorine interaction (Te1–Fi) 2.890 (2) Å) which is significantly shorter than the sum of the tellurium–fluorine van der Waals radii (3.53 Å, Bondi 1964).
For related literature, see: Beckmann et al. (2005); Bondi (1964); Hammerl et al. (2007).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. Molecular structure of [(2-Me2NCH2C6H4)2TeOH]2SiF6 with displacement ellipsoids drawn at the 50% probability level, solvent molecules not shown. Symmetry code: (i) 2 - x, -y, 2 - z. |
2C18H25N2OTe+·F6Si2−·4CHCl3 | F(000) = 1428 |
Mr = 1445.56 | Dx = 1.711 (1) Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 10976 reflections |
a = 9.3260 (2) Å | θ = 3.8–30.0° |
b = 26.7485 (5) Å | µ = 1.69 mm−1 |
c = 12.1579 (3) Å | T = 100 K |
β = 112.310 (3)° | Block, colourless |
V = 2805.84 (12) Å3 | 0.27 × 0.17 × 0.16 mm |
Z = 2 |
Oxford Xcalibur3 CCD area-detector diffractometer | 5303 independent reflections |
Radiation source: fine-focus sealed tube | 4543 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 15.9809 pixels mm-1 | θmax = 26.0°, θmin = 3.8° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −32→32 |
Tmin = 0.682, Tmax = 0.760 | l = −15→14 |
12419 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) = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0248P)2 + 1.7973P] where P = (Fo2 + 2Fc2)/3 |
5303 reflections | (Δ/σ)max = 0.002 |
316 parameters | Δρmax = 0.70 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
2C18H25N2OTe+·F6Si2−·4CHCl3 | V = 2805.84 (12) Å3 |
Mr = 1445.56 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.3260 (2) Å | µ = 1.69 mm−1 |
b = 26.7485 (5) Å | T = 100 K |
c = 12.1579 (3) Å | 0.27 × 0.17 × 0.16 mm |
β = 112.310 (3)° |
Oxford Xcalibur3 CCD area-detector diffractometer | 5303 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 4543 reflections with I > 2σ(I) |
Tmin = 0.682, Tmax = 0.760 | Rint = 0.020 |
12419 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.70 e Å−3 |
5303 reflections | Δρmin = −0.47 e Å−3 |
316 parameters |
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. Details of H atom refinement: H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C–H = 0.95 (CaromH), 1.00 (CH), 0.99 (CH2), 0.98 Å (CH3) and with Uiso(H) = kUeq(carrier atom), where k = 1.2 for CH2 and CH, and 1.5 for CH3. Atom H1 was located in a difference Fourier map and the position refined with the restraint O–H = 0.84 Å. The highest peak and deepest hole in the final difference map were located 0.82 and 0.77 Å, respectively, from atom Cl6. |
x | y | z | Uiso*/Ueq | ||
Te1 | 0.657332 (16) | 0.106265 (5) | 0.882461 (12) | 0.01500 (5) | |
N2 | 0.3736 (2) | 0.08058 (7) | 0.82241 (16) | 0.0177 (4) | |
N1 | 0.7151 (2) | 0.13877 (7) | 0.69141 (17) | 0.0211 (4) | |
C14 | 0.4448 (3) | 0.08912 (9) | 1.1451 (2) | 0.0234 (5) | |
H14 | 0.3442 | 0.0823 | 1.1437 | 0.028* | |
O1 | 0.86846 (18) | 0.13175 (6) | 0.96468 (14) | 0.0206 (3) | |
C16 | 0.3275 (3) | 0.09072 (9) | 0.9225 (2) | 0.0210 (5) | |
H16A | 0.2564 | 0.0641 | 0.9270 | 0.025* | |
H16B | 0.2706 | 0.1229 | 0.9088 | 0.025* | |
C13 | 0.5689 (3) | 0.09495 (9) | 1.2530 (2) | 0.0256 (5) | |
H13 | 0.5528 | 0.0921 | 1.3251 | 0.031* | |
C1 | 0.5838 (2) | 0.18220 (8) | 0.84948 (19) | 0.0161 (4) | |
C9 | 0.5761 (3) | 0.12922 (10) | 0.5851 (2) | 0.0281 (6) | |
H9A | 0.5643 | 0.0931 | 0.5704 | 0.042* | |
H9B | 0.5858 | 0.1459 | 0.5168 | 0.042* | |
H9C | 0.4847 | 0.1422 | 0.5967 | 0.042* | |
C6 | 0.6282 (3) | 0.21139 (9) | 0.7725 (2) | 0.0199 (5) | |
C18 | 0.2607 (3) | 0.10074 (10) | 0.7101 (2) | 0.0278 (6) | |
H18A | 0.2953 | 0.0933 | 0.6455 | 0.042* | |
H18B | 0.2526 | 0.1370 | 0.7171 | 0.042* | |
H18C | 0.1588 | 0.0854 | 0.6927 | 0.042* | |
C17 | 0.3917 (3) | 0.02619 (9) | 0.8115 (2) | 0.0274 (6) | |
H17A | 0.4229 | 0.0196 | 0.7448 | 0.041* | |
H17B | 0.2927 | 0.0094 | 0.7974 | 0.041* | |
H17C | 0.4716 | 0.0134 | 0.8851 | 0.041* | |
C7 | 0.7367 (3) | 0.19189 (9) | 0.7170 (2) | 0.0221 (5) | |
H7A | 0.7180 | 0.2103 | 0.6423 | 0.026* | |
H7B | 0.8455 | 0.1981 | 0.7718 | 0.026* | |
C10 | 0.6168 (3) | 0.10249 (8) | 1.0427 (2) | 0.0166 (4) | |
C4 | 0.4903 (3) | 0.28133 (9) | 0.8102 (2) | 0.0283 (6) | |
H4 | 0.4561 | 0.3150 | 0.7949 | 0.034* | |
C5 | 0.5788 (3) | 0.26103 (9) | 0.7539 (2) | 0.0267 (5) | |
H5 | 0.6070 | 0.2812 | 0.7012 | 0.032* | |
C12 | 0.7166 (3) | 0.10490 (9) | 1.2563 (2) | 0.0255 (5) | |
H12 | 0.8009 | 0.1095 | 1.3305 | 0.031* | |
C8 | 0.8526 (3) | 0.11594 (10) | 0.6818 (3) | 0.0317 (6) | |
H8A | 0.8338 | 0.0802 | 0.6648 | 0.048* | |
H8B | 0.9423 | 0.1203 | 0.7569 | 0.048* | |
H8C | 0.8736 | 0.1320 | 0.6174 | 0.048* | |
C11 | 0.7411 (3) | 0.10819 (9) | 1.1516 (2) | 0.0222 (5) | |
H11 | 0.8426 | 0.1143 | 1.1540 | 0.027* | |
C15 | 0.4664 (3) | 0.09319 (8) | 1.0388 (2) | 0.0179 (5) | |
C2 | 0.4969 (3) | 0.20344 (8) | 0.9081 (2) | 0.0201 (5) | |
H2 | 0.4690 | 0.1838 | 0.9617 | 0.024* | |
C3 | 0.4509 (3) | 0.25304 (9) | 0.8888 (2) | 0.0253 (5) | |
H3 | 0.3924 | 0.2675 | 0.9295 | 0.030* | |
Si1 | 1.0000 | 0.0000 | 1.0000 | 0.01539 (18) | |
F1 | 1.07064 (15) | 0.05684 (5) | 1.06107 (11) | 0.0210 (3) | |
F2 | 1.17733 (16) | −0.01661 (5) | 1.00741 (14) | 0.0320 (3) | |
F3 | 1.04137 (18) | −0.02414 (5) | 1.13490 (12) | 0.0310 (3) | |
Cl4 | 0.97905 (14) | 0.29009 (3) | 0.96386 (8) | 0.0668 (3) | |
Cl6 | 1.18389 (9) | 0.20509 (4) | 1.02213 (8) | 0.0558 (2) | |
C20 | 1.0230 (3) | 0.23273 (10) | 1.0382 (2) | 0.0285 (6) | |
H20 | 0.9316 | 0.2100 | 1.0020 | 0.034* | |
Cl2 | 0.18542 (8) | 0.11551 (2) | 0.34050 (7) | 0.03729 (16) | |
Cl3 | 0.34958 (8) | 0.02133 (3) | 0.38681 (7) | 0.03718 (16) | |
Cl5 | 1.05725 (9) | 0.24076 (3) | 1.18901 (6) | 0.0486 (2) | |
Cl1 | 0.05482 (9) | 0.02905 (3) | 0.40971 (7) | 0.04611 (19) | |
C19 | 0.1657 (3) | 0.05000 (9) | 0.3308 (2) | 0.0237 (5) | |
H19 | 0.1112 | 0.0405 | 0.2453 | 0.028* | |
H1 | 0.930 (3) | 0.1078 (7) | 0.992 (2) | 0.031 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Te1 | 0.01481 (8) | 0.01247 (8) | 0.01868 (8) | 0.00000 (6) | 0.00752 (6) | 0.00070 (6) |
N2 | 0.0176 (10) | 0.0158 (10) | 0.0204 (9) | −0.0004 (8) | 0.0082 (8) | −0.0016 (8) |
N1 | 0.0251 (11) | 0.0199 (10) | 0.0217 (10) | 0.0011 (8) | 0.0129 (9) | 0.0021 (8) |
C14 | 0.0322 (14) | 0.0148 (11) | 0.0296 (13) | 0.0004 (10) | 0.0191 (11) | 0.0003 (10) |
O1 | 0.0148 (8) | 0.0165 (8) | 0.0285 (9) | 0.0005 (7) | 0.0062 (7) | 0.0028 (7) |
C16 | 0.0189 (12) | 0.0194 (12) | 0.0273 (12) | −0.0010 (9) | 0.0119 (10) | −0.0011 (10) |
C13 | 0.0403 (15) | 0.0192 (12) | 0.0217 (12) | 0.0033 (11) | 0.0168 (11) | −0.0011 (10) |
C1 | 0.0150 (11) | 0.0133 (11) | 0.0171 (11) | 0.0000 (8) | 0.0030 (9) | 0.0010 (9) |
C9 | 0.0355 (15) | 0.0259 (13) | 0.0232 (12) | −0.0027 (11) | 0.0117 (11) | −0.0026 (11) |
C6 | 0.0198 (12) | 0.0191 (11) | 0.0175 (11) | −0.0037 (9) | 0.0036 (9) | 0.0008 (9) |
C18 | 0.0191 (12) | 0.0390 (15) | 0.0220 (12) | −0.0011 (11) | 0.0044 (10) | 0.0006 (11) |
C17 | 0.0305 (14) | 0.0168 (12) | 0.0392 (15) | −0.0064 (10) | 0.0182 (12) | −0.0068 (11) |
C7 | 0.0261 (13) | 0.0193 (12) | 0.0223 (12) | −0.0038 (10) | 0.0110 (10) | 0.0028 (10) |
C10 | 0.0216 (11) | 0.0107 (10) | 0.0199 (11) | 0.0028 (9) | 0.0105 (9) | 0.0019 (9) |
C4 | 0.0368 (15) | 0.0127 (11) | 0.0327 (14) | 0.0026 (10) | 0.0105 (12) | 0.0019 (10) |
C5 | 0.0353 (14) | 0.0175 (12) | 0.0255 (12) | −0.0035 (11) | 0.0098 (11) | 0.0053 (10) |
C12 | 0.0358 (14) | 0.0199 (12) | 0.0179 (11) | 0.0015 (11) | 0.0073 (11) | −0.0021 (10) |
C8 | 0.0366 (15) | 0.0326 (15) | 0.0355 (15) | 0.0094 (12) | 0.0246 (13) | 0.0085 (12) |
C11 | 0.0223 (12) | 0.0179 (12) | 0.0251 (12) | 0.0018 (10) | 0.0078 (10) | −0.0002 (10) |
C15 | 0.0223 (12) | 0.0099 (10) | 0.0230 (12) | 0.0005 (9) | 0.0106 (10) | 0.0003 (9) |
C2 | 0.0199 (12) | 0.0167 (11) | 0.0236 (12) | −0.0004 (9) | 0.0082 (10) | 0.0021 (9) |
C3 | 0.0291 (14) | 0.0165 (12) | 0.0303 (13) | 0.0017 (10) | 0.0115 (11) | −0.0026 (10) |
Si1 | 0.0146 (4) | 0.0148 (4) | 0.0151 (4) | 0.0008 (3) | 0.0038 (3) | 0.0011 (3) |
F1 | 0.0208 (7) | 0.0178 (7) | 0.0202 (7) | 0.0000 (5) | 0.0032 (6) | 0.0005 (5) |
F2 | 0.0208 (8) | 0.0208 (7) | 0.0573 (10) | 0.0026 (6) | 0.0183 (7) | 0.0015 (7) |
F3 | 0.0509 (10) | 0.0212 (7) | 0.0166 (7) | −0.0042 (7) | 0.0084 (7) | 0.0035 (6) |
Cl4 | 0.1229 (9) | 0.0308 (4) | 0.0442 (5) | 0.0042 (5) | 0.0295 (5) | 0.0048 (3) |
Cl6 | 0.0359 (4) | 0.0773 (6) | 0.0648 (5) | −0.0022 (4) | 0.0311 (4) | −0.0307 (5) |
C20 | 0.0310 (14) | 0.0265 (13) | 0.0319 (14) | −0.0031 (11) | 0.0165 (12) | −0.0046 (11) |
Cl2 | 0.0358 (4) | 0.0240 (3) | 0.0439 (4) | −0.0009 (3) | 0.0063 (3) | −0.0025 (3) |
Cl3 | 0.0264 (3) | 0.0305 (3) | 0.0503 (4) | 0.0026 (3) | 0.0101 (3) | 0.0028 (3) |
Cl5 | 0.0502 (5) | 0.0688 (5) | 0.0305 (4) | 0.0299 (4) | 0.0197 (3) | 0.0049 (4) |
Cl1 | 0.0460 (4) | 0.0547 (5) | 0.0493 (4) | −0.0008 (4) | 0.0312 (4) | 0.0102 (4) |
C19 | 0.0254 (13) | 0.0230 (13) | 0.0216 (12) | −0.0005 (10) | 0.0077 (10) | 0.0011 (10) |
Te1—O1 | 1.9612 (17) | C17—H17C | 0.9800 |
Te1—C10 | 2.123 (2) | C7—H7A | 0.9900 |
Te1—C1 | 2.132 (2) | C7—H7B | 0.9900 |
Te1—N2 | 2.557 (2) | C10—C11 | 1.398 (3) |
Te1—N1 | 2.719 (3) | C10—C15 | 1.407 (3) |
N2—C16 | 1.462 (3) | C4—C5 | 1.373 (4) |
N2—C18 | 1.474 (3) | C4—C3 | 1.378 (3) |
N2—C17 | 1.477 (3) | C4—H4 | 0.9500 |
N1—C7 | 1.452 (3) | C5—H5 | 0.9500 |
N1—C9 | 1.464 (3) | C12—C11 | 1.379 (3) |
N1—C8 | 1.465 (3) | C12—H12 | 0.9500 |
C14—C13 | 1.390 (3) | C8—H8A | 0.9800 |
C14—C15 | 1.386 (3) | C8—H8B | 0.9800 |
C14—H14 | 0.9500 | C8—H8C | 0.9800 |
O1—H1 | 0.84 (2) | C11—H11 | 0.9500 |
C16—C15 | 1.514 (3) | C2—C3 | 1.386 (3) |
C16—H16A | 0.9900 | C2—H2 | 0.9500 |
C16—H16B | 0.9900 | C3—H3 | 0.9500 |
C13—C12 | 1.388 (4) | Si1—F3i | 1.6659 (14) |
C13—H13 | 0.9500 | Si1—F3 | 1.6659 (14) |
C1—C2 | 1.388 (3) | Si1—F2 | 1.6808 (13) |
C1—C6 | 1.397 (3) | Si1—F2i | 1.6808 (13) |
C9—H9A | 0.9800 | Si1—F1i | 1.7091 (13) |
C9—H9B | 0.9800 | Si1—F1 | 1.7091 (13) |
C9—H9C | 0.9800 | Cl4—C20 | 1.748 (3) |
C6—C5 | 1.395 (3) | Cl6—C20 | 1.750 (3) |
C6—C7 | 1.511 (3) | C20—Cl5 | 1.751 (2) |
C18—H18A | 0.9800 | C20—H20 | 1.0000 |
C18—H18B | 0.9800 | Cl2—C19 | 1.761 (2) |
C18—H18C | 0.9800 | Cl3—C19 | 1.762 (3) |
C17—H17A | 0.9800 | Cl1—C19 | 1.748 (3) |
C17—H17B | 0.9800 | C19—H19 | 1.0000 |
O1—Te1—C10 | 92.46 (9) | C6—C7—H7A | 109.2 |
O1—Te1—C1 | 87.35 (7) | N1—C7—H7B | 109.2 |
C10—Te1—C1 | 93.44 (8) | C6—C7—H7B | 109.2 |
O1—Te1—N2 | 165.62 (6) | H7A—C7—H7B | 107.9 |
C10—Te1—N2 | 73.97 (8) | C11—C10—C15 | 120.6 (2) |
C1—Te1—N2 | 88.75 (7) | C11—C10—Te1 | 119.44 (17) |
O1—Te1—N2 | 165.62 (6) | C15—C10—Te1 | 119.99 (17) |
C10—Te1—N2 | 73.97 (8) | C5—C4—C3 | 120.0 (2) |
C1—Te1—N2 | 88.75 (7) | C5—C4—H4 | 119.9 |
O1—Te1—N1 | 80.68 (6) | C3—C4—H4 | 119.9 |
C10—Te1—N1 | 163.99 (7) | C4—C5—C6 | 121.3 (2) |
C1—Te1—N1 | 71.86 (7) | C4—C5—H5 | 119.3 |
N1—Te1—N2 | 111.17 (6) | C6—C5—H5 | 119.3 |
C16—N2—C18 | 111.85 (18) | C11—C12—C13 | 119.7 (2) |
C16—N2—C17 | 109.71 (18) | C11—C12—H12 | 120.0 |
C18—N2—C17 | 110.1 (2) | C13—C12—H12 | 120.0 |
C16—N2—Te1 | 108.18 (14) | N1—C8—H8A | 109.5 |
C18—N2—Te1 | 117.65 (15) | N1—C8—H8B | 109.5 |
C17—N2—Te1 | 98.58 (14) | H8A—C8—H8B | 109.5 |
C7—N1—C9 | 111.36 (19) | N1—C8—H8C | 109.5 |
C7—N1—C8 | 111.8 (2) | H8A—C8—H8C | 109.5 |
C9—N1—C8 | 111.2 (2) | H8B—C8—H8C | 109.5 |
C13—C14—C15 | 120.5 (2) | C12—C11—C10 | 119.9 (2) |
C13—C14—H14 | 119.7 | C12—C11—H11 | 120.0 |
C15—C14—H14 | 119.7 | C10—C11—H11 | 120.0 |
Te1—O1—H1 | 110 (2) | C14—C15—C10 | 118.6 (2) |
N2—C16—C15 | 111.64 (18) | C14—C15—C16 | 119.5 (2) |
N2—C16—H16A | 109.3 | C10—C15—C16 | 121.9 (2) |
C15—C16—H16A | 109.3 | C3—C2—C1 | 120.4 (2) |
N2—C16—H16B | 109.3 | C3—C2—H2 | 119.8 |
C15—C16—H16B | 109.3 | C1—C2—H2 | 119.8 |
H16A—C16—H16B | 108.0 | C4—C3—C2 | 119.7 (2) |
C14—C13—C12 | 120.7 (2) | C4—C3—H3 | 120.1 |
C14—C13—H13 | 119.9 | C2—C3—H3 | 120.1 |
C12—C13—H13 | 119.9 | F3i—Si1—F3 | 180.0 |
C2—C1—C6 | 119.9 (2) | F3i—Si1—F2 | 90.61 (8) |
C2—C1—Te1 | 120.04 (16) | F3—Si1—F2 | 89.39 (8) |
C6—C1—Te1 | 120.04 (16) | F3i—Si1—F2i | 89.39 (8) |
N1—C9—H9A | 109.5 | F3—Si1—F2i | 90.61 (8) |
N1—C9—H9B | 109.5 | F2—Si1—F2i | 180.0 |
H9A—C9—H9B | 109.5 | F3i—Si1—F1i | 90.58 (6) |
N1—C9—H9C | 109.5 | F3—Si1—F1i | 89.42 (6) |
H9A—C9—H9C | 109.5 | F2—Si1—F1i | 89.85 (7) |
H9B—C9—H9C | 109.5 | F2i—Si1—F1i | 90.16 (7) |
C5—C6—C1 | 118.4 (2) | F3i—Si1—F1 | 89.42 (6) |
C5—C6—C7 | 119.5 (2) | F3—Si1—F1 | 90.58 (6) |
C1—C6—C7 | 122.0 (2) | F2—Si1—F1 | 90.16 (7) |
N2—C18—H18A | 109.5 | F2i—Si1—F1 | 89.85 (7) |
N2—C18—H18B | 109.5 | F1i—Si1—F1 | 180.00 (4) |
H18A—C18—H18B | 109.5 | Cl4—C20—Cl6 | 110.85 (16) |
N2—C18—H18C | 109.5 | Cl4—C20—Cl5 | 110.32 (14) |
H18A—C18—H18C | 109.5 | Cl6—C20—Cl5 | 110.22 (14) |
H18B—C18—H18C | 109.5 | Cl4—C20—H20 | 108.4 |
N2—C17—H17A | 109.5 | Cl6—C20—H20 | 108.4 |
N2—C17—H17B | 109.5 | Cl5—C20—H20 | 108.4 |
H17A—C17—H17B | 109.5 | Cl1—C19—Cl3 | 109.93 (13) |
N2—C17—H17C | 109.5 | Cl1—C19—Cl2 | 110.45 (13) |
H17A—C17—H17C | 109.5 | Cl3—C19—Cl2 | 110.30 (13) |
H17B—C17—H17C | 109.5 | Cl1—C19—H19 | 108.7 |
N1—C7—C6 | 111.86 (19) | Cl3—C19—H19 | 108.7 |
N1—C7—H7A | 109.2 | Cl2—C19—H19 | 108.7 |
O1—Te1—N2—C16 | −4.3 (3) | C1—C6—C7—N1 | 34.1 (3) |
C10—Te1—N2—C16 | 15.43 (14) | O1—Te1—C10—C11 | −11.54 (18) |
C1—Te1—N2—C16 | −78.50 (14) | C1—Te1—C10—C11 | −98.90 (18) |
O1—Te1—N2—C18 | 123.6 (3) | N2—Te1—C10—C11 | 173.30 (19) |
C10—Te1—N2—C18 | 143.28 (17) | O1—Te1—C10—C15 | 169.89 (17) |
C1—Te1—N2—C18 | 49.36 (17) | C1—Te1—C10—C15 | 82.53 (18) |
O1—Te1—N2—C17 | −118.5 (3) | N2—Te1—C10—C15 | −5.27 (16) |
C10—Te1—N2—C17 | −98.76 (15) | C3—C4—C5—C6 | 1.3 (4) |
C1—Te1—N2—C17 | 167.31 (15) | C1—C6—C5—C4 | 0.7 (4) |
C18—N2—C16—C15 | −153.0 (2) | C7—C6—C5—C4 | −174.8 (2) |
C17—N2—C16—C15 | 84.5 (2) | C14—C13—C12—C11 | −1.1 (4) |
Te1—N2—C16—C15 | −22.1 (2) | C13—C12—C11—C10 | 1.3 (3) |
C15—C14—C13—C12 | −0.1 (4) | C15—C10—C11—C12 | −0.2 (3) |
O1—Te1—C1—C2 | −109.56 (18) | Te1—C10—C11—C12 | −178.82 (17) |
C10—Te1—C1—C2 | −17.04 (18) | C13—C14—C15—C10 | 1.1 (3) |
N2—Te1—C1—C2 | 56.51 (18) | C13—C14—C15—C16 | −175.2 (2) |
O1—Te1—C1—C6 | 67.85 (18) | C11—C10—C15—C14 | −0.9 (3) |
C10—Te1—C1—C6 | 160.37 (18) | Te1—C10—C15—C14 | 177.65 (16) |
N2—Te1—C1—C6 | −126.08 (18) | C11—C10—C15—C16 | 175.3 (2) |
C2—C1—C6—C5 | −2.1 (3) | Te1—C10—C15—C16 | −6.1 (3) |
Te1—C1—C6—C5 | −179.50 (17) | N2—C16—C15—C14 | −162.94 (19) |
C2—C1—C6—C7 | 173.3 (2) | N2—C16—C15—C10 | 20.9 (3) |
Te1—C1—C6—C7 | −4.1 (3) | C6—C1—C2—C3 | 1.5 (3) |
C9—N1—C7—C6 | 76.6 (2) | Te1—C1—C2—C3 | 178.88 (18) |
C8—N1—C7—C6 | −158.1 (2) | C5—C4—C3—C2 | −2.0 (4) |
C5—C6—C7—N1 | −150.6 (2) | C1—C2—C3—C4 | 0.6 (4) |
Symmetry code: (i) −x+2, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···F1 | 0.84 (2) | 1.86 (2) | 2.696 (2) | 177 (3) |
Experimental details
Crystal data | |
Chemical formula | 2C18H25N2OTe+·F6Si2−·4CHCl3 |
Mr | 1445.56 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 9.3260 (2), 26.7485 (5), 12.1579 (3) |
β (°) | 112.310 (3) |
V (Å3) | 2805.84 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.69 |
Crystal size (mm) | 0.27 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Oxford Xcalibur3 CCD area-detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.682, 0.760 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12419, 5303, 4543 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.022, 0.053, 1.04 |
No. of reflections | 5303 |
No. of parameters | 316 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.70, −0.47 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···F1 | 0.84 (2) | 1.86 (2) | 2.696 (2) | 177 (3) |
As part of our recent studies regarding tellurium(II) and tellurium(IV) compounds with the intramolecular donor stabilizing substituent 2-Me2NCH2C6H4 (Hammerl et al., 2007) we obtained the title compound as a decomposition product.
In the title compound two intramolecular interactions between the aminomethyl nitrogen atom and the tellurium atom create two five-membered heterocycles with a 4-coordinated amine moiety (Te1···N1 2.719 (3) and Te1···N2 2.557 (2) Å). The Te1–O1 distance is with 1.9612 (17) Å slightly elongated compared to the calculated bond distance in [Ph2TeOH]+ (1.937 Å, Beckmann et al., 2005). The present hydrogen bridge O1–H1···F1 links the cation with the anion and exhibits a donor acceptor distance of 2.696 (2) Å. The tellurium atom is further coordinated by an intermolecular tellurium–fluorine interaction (Te1–Fi) 2.890 (2) Å) which is significantly shorter than the sum of the tellurium–fluorine van der Waals radii (3.53 Å, Bondi 1964).