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Three novel chalcogen-bonded cocrystals featuring 3,4-dicyano-1,2,5-selenodiazole (C4N4Se) or 3,4-dicyano-1,2,5-tellurodiazole (C4N4Te) as chalcogen-bond donors and hydroquinone (C6H6O2), tetraphenylphosphonium chloride (C24H20P+·Cl−) or tetraethylphosphonium chloride (C8H20P+·Cl−) as chalcogen-bond acceptors have been prepared and characterized by single-crystal X-ray diffraction (XRD), powder X-ray diffraction and 77Se/125Te magic-angle spinning solid-state NMR spectroscopy. The single-crystal XRD results show that the chalcogenodiazole molecules interact with the electron donors through two σ-holes on each of the chalcogen atoms, which results in highly directional and moderately strong chalcogen bonds. Powder XRD confirms that the crystalline phases are preserved upon moderate grinding of the samples for solid-state NMR experiments. Measurement of 77Se and 125Te chemical shift tensors via magic-angle spinning solid-state NMR spectroscopy confirms the number of magnetically unique chalcogen sites in each asymmetric unit and reveals the impact of chalcogen-bond formation on the local electronic structure. These NMR data are further assessed in the context of analogous data for a wider range of crystalline chalcogen-bonded systems.
Supporting information
CCDC references: 2174994; 2174995; 2174993
For all structures, data collection: APEX3 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b).
1,2,5-Tellurodiazole-3,4-dicarbonitrile tetraphenylphosphonium chloride (2c)
top
Crystal data top
C4N4Te·C24H20P+·Cl− | F(000) = 1200 |
Mr = 606.50 | Dx = 1.575 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 18.2538 (5) Å | Cell parameters from 9980 reflections |
b = 7.3008 (2) Å | θ = 2.7–30.5° |
c = 20.0497 (5) Å | µ = 1.36 mm−1 |
β = 106.867 (2)° | T = 208 K |
V = 2557.02 (12) Å3 | Needle, yellow |
Z = 4 | 0.53 × 0.16 × 0.10 mm |
Data collection top
Bruker APEXII CCD diffractometer | 6408 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω and πhi scans | θmax = 30.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −26→26 |
Tmin = 0.665, Tmax = 0.746 | k = −10→6 |
58500 measured reflections | l = −28→28 |
7883 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.025P)2 + 1.3443P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.003 |
7883 reflections | Δρmax = 0.73 e Å−3 |
316 parameters | Δρmin = −0.49 e Å−3 |
0 restraints | |
Special details top
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. none |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Te1 | 0.76837 (2) | 0.11309 (2) | 0.40232 (2) | 0.03137 (4) | |
Cl1 | 0.82995 (4) | −0.21490 (8) | 0.44379 (4) | 0.06429 (18) | |
P1 | 0.53900 (2) | 0.50383 (6) | 0.79116 (2) | 0.02281 (8) | |
N1 | 0.63058 (15) | 0.2746 (4) | 0.59019 (11) | 0.0706 (7) | |
N2 | 0.73064 (9) | 0.0947 (2) | 0.48627 (7) | 0.0318 (3) | |
N3 | 0.71542 (9) | 0.3628 (2) | 0.38961 (8) | 0.0342 (3) | |
N4 | 0.60955 (13) | 0.6811 (3) | 0.44978 (12) | 0.0590 (5) | |
C1 | 0.65878 (13) | 0.2594 (3) | 0.54712 (10) | 0.0442 (5) | |
C2 | 0.69348 (10) | 0.2427 (3) | 0.49107 (8) | 0.0314 (4) | |
C3 | 0.68536 (10) | 0.3871 (2) | 0.43973 (9) | 0.0313 (3) | |
C4 | 0.64358 (12) | 0.5536 (3) | 0.44507 (10) | 0.0401 (4) | |
C5 | 0.51895 (9) | 0.6486 (2) | 0.71539 (8) | 0.0253 (3) | |
C6 | 0.54541 (11) | 0.6101 (3) | 0.65862 (9) | 0.0344 (4) | |
H6 | 0.574505 | 0.504130 | 0.658230 | 0.041* | |
C7 | 0.52839 (12) | 0.7302 (3) | 0.60231 (10) | 0.0443 (5) | |
H7 | 0.546203 | 0.704917 | 0.563739 | 0.053* | |
C8 | 0.48569 (12) | 0.8857 (3) | 0.60252 (10) | 0.0410 (4) | |
H8 | 0.475389 | 0.966937 | 0.564530 | 0.049* | |
C9 | 0.45806 (12) | 0.9228 (3) | 0.65808 (10) | 0.0374 (4) | |
H9 | 0.428044 | 1.027677 | 0.657644 | 0.045* | |
C10 | 0.47469 (11) | 0.8047 (3) | 0.71477 (9) | 0.0328 (4) | |
H10 | 0.456069 | 0.829996 | 0.752866 | 0.039* | |
C11 | 0.55642 (10) | 0.6521 (2) | 0.86513 (8) | 0.0263 (3) | |
C12 | 0.61184 (10) | 0.7894 (3) | 0.87283 (9) | 0.0318 (4) | |
H12 | 0.639206 | 0.801315 | 0.839924 | 0.038* | |
C13 | 0.62606 (11) | 0.9071 (2) | 0.92906 (10) | 0.0347 (4) | |
H13 | 0.663091 | 0.999740 | 0.934505 | 0.042* | |
C14 | 0.58572 (12) | 0.8883 (3) | 0.97730 (9) | 0.0373 (4) | |
H14 | 0.596101 | 0.967230 | 1.015969 | 0.045* | |
C15 | 0.53041 (12) | 0.7550 (3) | 0.96921 (9) | 0.0361 (4) | |
H15 | 0.502905 | 0.744533 | 1.002063 | 0.043* | |
C16 | 0.51505 (10) | 0.6361 (2) | 0.91292 (8) | 0.0294 (3) | |
H16 | 0.477067 | 0.545648 | 0.907234 | 0.035* | |
C17 | 0.45931 (9) | 0.3566 (2) | 0.78705 (8) | 0.0239 (3) | |
C18 | 0.38917 (10) | 0.3841 (2) | 0.73768 (9) | 0.0290 (3) | |
H18 | 0.382532 | 0.482650 | 0.706328 | 0.035* | |
C19 | 0.32895 (11) | 0.2660 (3) | 0.73467 (10) | 0.0375 (4) | |
H19 | 0.281645 | 0.282794 | 0.700683 | 0.045* | |
C20 | 0.33854 (12) | 0.1233 (3) | 0.78173 (11) | 0.0399 (4) | |
H20 | 0.297459 | 0.043856 | 0.779824 | 0.048* | |
C21 | 0.40827 (12) | 0.0964 (3) | 0.83176 (10) | 0.0367 (4) | |
H21 | 0.414100 | 0.000098 | 0.863990 | 0.044* | |
C22 | 0.46904 (10) | 0.2110 (2) | 0.83420 (8) | 0.0301 (3) | |
H22 | 0.516709 | 0.191474 | 0.867346 | 0.036* | |
C23 | 0.62056 (9) | 0.3594 (2) | 0.79919 (8) | 0.0269 (3) | |
C24 | 0.68523 (10) | 0.3713 (3) | 0.85649 (10) | 0.0370 (4) | |
H24 | 0.688031 | 0.458834 | 0.891513 | 0.044* | |
C25 | 0.74562 (12) | 0.2515 (3) | 0.86109 (13) | 0.0516 (6) | |
H25 | 0.789755 | 0.258960 | 0.899437 | 0.062* | |
C26 | 0.74176 (14) | 0.1230 (3) | 0.81068 (15) | 0.0553 (6) | |
H26 | 0.783276 | 0.043503 | 0.814499 | 0.066* | |
C27 | 0.67729 (14) | 0.1092 (3) | 0.75417 (13) | 0.0482 (5) | |
H27 | 0.675016 | 0.020198 | 0.719743 | 0.058* | |
C28 | 0.61616 (11) | 0.2258 (3) | 0.74808 (10) | 0.0348 (4) | |
H28 | 0.571945 | 0.215553 | 0.709940 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Te1 | 0.03376 (6) | 0.02925 (7) | 0.03059 (6) | 0.00399 (5) | 0.00851 (4) | 0.00111 (5) |
Cl1 | 0.0535 (3) | 0.0394 (3) | 0.1012 (5) | 0.0189 (3) | 0.0244 (3) | 0.0182 (3) |
P1 | 0.02465 (19) | 0.0229 (2) | 0.02068 (17) | 0.00148 (15) | 0.00630 (14) | −0.00144 (14) |
N1 | 0.0948 (18) | 0.0807 (17) | 0.0481 (11) | 0.0158 (14) | 0.0395 (12) | 0.0028 (11) |
N2 | 0.0339 (7) | 0.0317 (8) | 0.0268 (6) | 0.0013 (6) | 0.0042 (6) | 0.0045 (6) |
N3 | 0.0409 (8) | 0.0309 (8) | 0.0291 (7) | 0.0061 (7) | 0.0076 (6) | 0.0049 (6) |
N4 | 0.0655 (13) | 0.0429 (11) | 0.0709 (14) | 0.0170 (10) | 0.0235 (11) | 0.0014 (10) |
C1 | 0.0554 (13) | 0.0454 (12) | 0.0329 (9) | 0.0056 (10) | 0.0145 (9) | 0.0007 (8) |
C2 | 0.0347 (9) | 0.0339 (10) | 0.0237 (7) | 0.0006 (7) | 0.0054 (6) | 0.0000 (7) |
C3 | 0.0344 (9) | 0.0276 (9) | 0.0284 (8) | 0.0032 (7) | 0.0037 (6) | −0.0005 (7) |
C4 | 0.0451 (11) | 0.0361 (10) | 0.0374 (9) | 0.0054 (9) | 0.0094 (8) | −0.0004 (8) |
C5 | 0.0265 (7) | 0.0252 (8) | 0.0233 (7) | −0.0005 (6) | 0.0059 (6) | −0.0003 (6) |
C6 | 0.0365 (9) | 0.0395 (10) | 0.0306 (8) | 0.0059 (8) | 0.0149 (7) | 0.0030 (8) |
C7 | 0.0471 (11) | 0.0583 (14) | 0.0317 (9) | 0.0030 (10) | 0.0181 (8) | 0.0081 (9) |
C8 | 0.0402 (10) | 0.0441 (11) | 0.0348 (9) | −0.0046 (9) | 0.0048 (8) | 0.0139 (8) |
C9 | 0.0402 (10) | 0.0267 (10) | 0.0398 (9) | 0.0026 (8) | 0.0030 (8) | 0.0043 (7) |
C10 | 0.0398 (10) | 0.0278 (9) | 0.0318 (8) | 0.0044 (8) | 0.0121 (7) | −0.0011 (7) |
C11 | 0.0307 (8) | 0.0245 (8) | 0.0222 (7) | 0.0012 (6) | 0.0054 (6) | −0.0021 (6) |
C12 | 0.0348 (9) | 0.0298 (9) | 0.0303 (8) | −0.0027 (7) | 0.0085 (7) | −0.0009 (7) |
C13 | 0.0369 (9) | 0.0248 (9) | 0.0357 (9) | −0.0024 (7) | −0.0003 (7) | −0.0018 (7) |
C14 | 0.0481 (11) | 0.0296 (9) | 0.0281 (8) | 0.0054 (8) | 0.0017 (7) | −0.0074 (7) |
C15 | 0.0479 (11) | 0.0353 (10) | 0.0266 (8) | 0.0048 (8) | 0.0131 (7) | −0.0039 (7) |
C16 | 0.0346 (9) | 0.0273 (9) | 0.0266 (7) | −0.0002 (7) | 0.0093 (6) | −0.0023 (6) |
C17 | 0.0271 (7) | 0.0217 (8) | 0.0234 (7) | 0.0020 (6) | 0.0083 (6) | −0.0021 (6) |
C18 | 0.0294 (8) | 0.0274 (8) | 0.0278 (7) | 0.0025 (7) | 0.0046 (6) | −0.0023 (7) |
C19 | 0.0281 (8) | 0.0389 (11) | 0.0440 (10) | −0.0021 (8) | 0.0082 (7) | −0.0122 (8) |
C20 | 0.0409 (10) | 0.0350 (10) | 0.0512 (11) | −0.0116 (8) | 0.0250 (9) | −0.0152 (9) |
C21 | 0.0548 (12) | 0.0265 (9) | 0.0358 (9) | −0.0017 (8) | 0.0243 (8) | −0.0008 (7) |
C22 | 0.0365 (9) | 0.0286 (9) | 0.0256 (7) | 0.0045 (7) | 0.0093 (7) | 0.0015 (6) |
C23 | 0.0246 (7) | 0.0275 (9) | 0.0290 (7) | 0.0026 (6) | 0.0082 (6) | 0.0024 (6) |
C24 | 0.0298 (9) | 0.0398 (11) | 0.0380 (9) | 0.0006 (8) | 0.0045 (7) | 0.0053 (8) |
C25 | 0.0282 (9) | 0.0591 (15) | 0.0628 (14) | 0.0097 (10) | 0.0056 (9) | 0.0166 (12) |
C26 | 0.0435 (12) | 0.0514 (14) | 0.0794 (17) | 0.0227 (11) | 0.0309 (12) | 0.0203 (12) |
C27 | 0.0575 (13) | 0.0364 (11) | 0.0617 (13) | 0.0156 (10) | 0.0348 (11) | 0.0056 (10) |
C28 | 0.0394 (10) | 0.0322 (10) | 0.0352 (9) | 0.0060 (8) | 0.0144 (7) | −0.0001 (7) |
Geometric parameters (Å, º) top
Te1—N2 | 1.9994 (15) | C13—C14 | 1.382 (3) |
Te1—N3 | 2.0448 (15) | C13—H13 | 0.9400 |
Te1—Cl1 | 2.6734 (6) | C14—C15 | 1.378 (3) |
P1—C11 | 1.7887 (16) | C14—H14 | 0.9400 |
P1—C17 | 1.7911 (17) | C15—C16 | 1.386 (2) |
P1—C23 | 1.7932 (17) | C15—H15 | 0.9400 |
P1—C5 | 1.7991 (16) | C16—H16 | 0.9400 |
N1—C1 | 1.132 (3) | C17—C18 | 1.387 (2) |
N2—C2 | 1.295 (2) | C17—C22 | 1.399 (2) |
N3—C3 | 1.289 (2) | C18—C19 | 1.384 (3) |
N4—C4 | 1.138 (3) | C18—H18 | 0.9400 |
C1—C2 | 1.446 (3) | C19—C20 | 1.382 (3) |
C2—C3 | 1.451 (2) | C19—H19 | 0.9400 |
C3—C4 | 1.455 (3) | C20—C21 | 1.387 (3) |
C5—C6 | 1.388 (2) | C20—H20 | 0.9400 |
C5—C10 | 1.395 (2) | C21—C22 | 1.379 (3) |
C6—C7 | 1.391 (3) | C21—H21 | 0.9400 |
C6—H6 | 0.9400 | C22—H22 | 0.9400 |
C7—C8 | 1.378 (3) | C23—C24 | 1.391 (2) |
C7—H7 | 0.9400 | C23—C28 | 1.400 (2) |
C8—C9 | 1.377 (3) | C24—C25 | 1.389 (3) |
C8—H8 | 0.9400 | C24—H24 | 0.9400 |
C9—C10 | 1.388 (3) | C25—C26 | 1.366 (4) |
C9—H9 | 0.9400 | C25—H25 | 0.9400 |
C10—H10 | 0.9400 | C26—C27 | 1.380 (4) |
C11—C16 | 1.386 (2) | C26—H26 | 0.9400 |
C11—C12 | 1.400 (2) | C27—C28 | 1.380 (3) |
C12—C13 | 1.381 (3) | C27—H27 | 0.9400 |
C12—H12 | 0.9400 | C28—H28 | 0.9400 |
| | | |
N2—Te1—N3 | 84.21 (6) | C15—C14—C13 | 120.57 (17) |
N2—Te1—Cl1 | 83.93 (5) | C15—C14—H14 | 119.7 |
N3—Te1—Cl1 | 168.08 (5) | C13—C14—H14 | 119.7 |
C11—P1—C17 | 110.37 (8) | C14—C15—C16 | 120.43 (17) |
C11—P1—C23 | 109.77 (8) | C14—C15—H15 | 119.8 |
C17—P1—C23 | 107.06 (8) | C16—C15—H15 | 119.8 |
C11—P1—C5 | 106.75 (8) | C11—C16—C15 | 119.18 (17) |
C17—P1—C5 | 110.50 (7) | C11—C16—H16 | 120.4 |
C23—P1—C5 | 112.42 (8) | C15—C16—H16 | 120.4 |
C2—N2—Te1 | 108.80 (11) | C18—C17—C22 | 120.13 (16) |
C3—N3—Te1 | 108.54 (12) | C18—C17—P1 | 121.02 (13) |
N1—C1—C2 | 178.7 (3) | C22—C17—P1 | 118.85 (13) |
N2—C2—C1 | 119.02 (17) | C19—C18—C17 | 119.86 (17) |
N2—C2—C3 | 120.12 (16) | C19—C18—H18 | 120.1 |
C1—C2—C3 | 120.84 (17) | C17—C18—H18 | 120.1 |
N3—C3—C2 | 118.32 (16) | C20—C19—C18 | 119.86 (18) |
N3—C3—C4 | 121.52 (17) | C20—C19—H19 | 120.1 |
C2—C3—C4 | 120.16 (16) | C18—C19—H19 | 120.1 |
N4—C4—C3 | 178.2 (2) | C19—C20—C21 | 120.54 (18) |
C6—C5—C10 | 119.77 (16) | C19—C20—H20 | 119.7 |
C6—C5—P1 | 122.66 (13) | C21—C20—H20 | 119.7 |
C10—C5—P1 | 117.57 (12) | C22—C21—C20 | 119.99 (18) |
C5—C6—C7 | 119.28 (18) | C22—C21—H21 | 120.0 |
C5—C6—H6 | 120.4 | C20—C21—H21 | 120.0 |
C7—C6—H6 | 120.4 | C21—C22—C17 | 119.59 (17) |
C8—C7—C6 | 120.66 (18) | C21—C22—H22 | 120.2 |
C8—C7—H7 | 119.7 | C17—C22—H22 | 120.2 |
C6—C7—H7 | 119.7 | C24—C23—C28 | 120.18 (17) |
C9—C8—C7 | 120.32 (18) | C24—C23—P1 | 121.41 (14) |
C9—C8—H8 | 119.8 | C28—C23—P1 | 118.31 (13) |
C7—C8—H8 | 119.8 | C25—C24—C23 | 118.9 (2) |
C8—C9—C10 | 119.74 (18) | C25—C24—H24 | 120.6 |
C8—C9—H9 | 120.1 | C23—C24—H24 | 120.6 |
C10—C9—H9 | 120.1 | C26—C25—C24 | 120.9 (2) |
C9—C10—C5 | 120.21 (17) | C26—C25—H25 | 119.5 |
C9—C10—H10 | 119.9 | C24—C25—H25 | 119.5 |
C5—C10—H10 | 119.9 | C25—C26—C27 | 120.4 (2) |
C16—C11—C12 | 120.36 (15) | C25—C26—H26 | 119.8 |
C16—C11—P1 | 121.35 (13) | C27—C26—H26 | 119.8 |
C12—C11—P1 | 118.27 (13) | C26—C27—C28 | 120.1 (2) |
C13—C12—C11 | 119.60 (17) | C26—C27—H27 | 119.9 |
C13—C12—H12 | 120.2 | C28—C27—H27 | 119.9 |
C11—C12—H12 | 120.2 | C27—C28—C23 | 119.45 (19) |
C12—C13—C14 | 119.84 (18) | C27—C28—H28 | 120.3 |
C12—C13—H13 | 120.1 | C23—C28—H28 | 120.3 |
C14—C13—H13 | 120.1 | | |
| | | |
Te1—N2—C2—C1 | 178.40 (15) | C13—C14—C15—C16 | 0.8 (3) |
Te1—N2—C2—C3 | 0.0 (2) | C12—C11—C16—C15 | −1.4 (3) |
Te1—N3—C3—C2 | −0.7 (2) | P1—C11—C16—C15 | −179.64 (14) |
Te1—N3—C3—C4 | 179.86 (15) | C14—C15—C16—C11 | 0.5 (3) |
N2—C2—C3—N3 | 0.5 (3) | C11—P1—C17—C18 | 106.65 (14) |
C1—C2—C3—N3 | −177.89 (18) | C23—P1—C17—C18 | −133.92 (14) |
N2—C2—C3—C4 | 179.99 (17) | C5—P1—C17—C18 | −11.18 (16) |
C1—C2—C3—C4 | 1.6 (3) | C11—P1—C17—C22 | −74.06 (14) |
C11—P1—C5—C6 | 140.98 (15) | C23—P1—C17—C22 | 45.37 (14) |
C17—P1—C5—C6 | −98.98 (16) | C5—P1—C17—C22 | 168.10 (12) |
C23—P1—C5—C6 | 20.56 (18) | C22—C17—C18—C19 | −0.6 (2) |
C11—P1—C5—C10 | −39.24 (16) | P1—C17—C18—C19 | 178.63 (13) |
C17—P1—C5—C10 | 80.79 (15) | C17—C18—C19—C20 | 1.2 (3) |
C23—P1—C5—C10 | −159.66 (14) | C18—C19—C20—C21 | −0.5 (3) |
C10—C5—C6—C7 | 1.1 (3) | C19—C20—C21—C22 | −0.9 (3) |
P1—C5—C6—C7 | −179.11 (16) | C20—C21—C22—C17 | 1.5 (3) |
C5—C6—C7—C8 | −0.1 (3) | C18—C17—C22—C21 | −0.7 (2) |
C6—C7—C8—C9 | −1.2 (3) | P1—C17—C22—C21 | 179.99 (13) |
C7—C8—C9—C10 | 1.3 (3) | C11—P1—C23—C24 | −0.02 (17) |
C8—C9—C10—C5 | −0.3 (3) | C17—P1—C23—C24 | −119.83 (15) |
C6—C5—C10—C9 | −1.0 (3) | C5—P1—C23—C24 | 118.64 (15) |
P1—C5—C10—C9 | 179.26 (15) | C11—P1—C23—C28 | 176.35 (14) |
C17—P1—C11—C16 | 4.56 (17) | C17—P1—C23—C28 | 56.53 (15) |
C23—P1—C11—C16 | −113.21 (15) | C5—P1—C23—C28 | −64.99 (16) |
C5—P1—C11—C16 | 124.68 (14) | C28—C23—C24—C25 | 1.5 (3) |
C17—P1—C11—C12 | −173.73 (13) | P1—C23—C24—C25 | 177.76 (16) |
C23—P1—C11—C12 | 68.50 (15) | C23—C24—C25—C26 | −0.5 (3) |
C5—P1—C11—C12 | −53.61 (15) | C24—C25—C26—C27 | −0.3 (4) |
C16—C11—C12—C13 | 1.1 (3) | C25—C26—C27—C28 | 0.2 (4) |
P1—C11—C12—C13 | 179.39 (14) | C26—C27—C28—C23 | 0.8 (3) |
C11—C12—C13—C14 | 0.2 (3) | C24—C23—C28—C27 | −1.6 (3) |
C12—C13—C14—C15 | −1.1 (3) | P1—C23—C28—C27 | −178.06 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···N1 | 0.94 | 2.55 | 3.397 (3) | 149 |
C18—H18···N3i | 0.94 | 2.48 | 3.278 (2) | 142 |
C24—H24···N2ii | 0.94 | 2.66 | 3.485 (2) | 147 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, −z+3/2. |
1,2,5-Tellurodiazole-3,4-dicarbonitrile tetraethylphosphonium chloride (2b)
top
Crystal data top
C4N4Te·C8H20P+·Cl− | Z = 2 |
Mr = 414.34 | F(000) = 408 |
Triclinic, P1 | Dx = 1.593 Mg m−3 |
a = 6.9500 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5921 (15) Å | Cell parameters from 9536 reflections |
c = 13.604 (2) Å | θ = 2.2–30.5° |
α = 102.427 (2)° | µ = 1.96 mm−1 |
β = 101.890 (2)° | T = 213 K |
γ = 91.876 (2)° | Plate, yellow |
V = 863.8 (2) Å3 | 0.72 × 0.35 × 0.31 mm |
Data collection top
Bruker APEXII CCD diffractometer | 5740 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω and πhi scans | θmax = 32.7°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −10→10 |
Tmin = 0.617, Tmax = 0.746 | k = −14→14 |
20481 measured reflections | l = −20→19 |
5948 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0118P)2 + 3.3734P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
5948 reflections | Δρmax = 2.00 e Å−3 |
179 parameters | Δρmin = −1.44 e Å−3 |
0 restraints | |
Special details top
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. none |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Te1 | 0.09776 (3) | 0.78751 (2) | 0.14068 (2) | 0.02687 (6) | |
Cl1 | 0.000000 | 0.500000 | 0.000000 | 0.0513 (4) | |
Cl2 | 0.000000 | 0.000000 | 0.000000 | 0.0631 (5) | |
P1 | 0.69352 (14) | 0.30361 (10) | 0.21843 (7) | 0.03072 (17) | |
N1 | 0.1463 (5) | 0.9557 (3) | 0.2638 (2) | 0.0342 (6) | |
N2 | 0.1952 (5) | 0.6719 (3) | 0.2462 (2) | 0.0330 (6) | |
N3 | 0.2738 (9) | 1.0727 (6) | 0.5311 (4) | 0.0741 (15) | |
N4 | 0.3786 (10) | 0.6562 (6) | 0.4970 (4) | 0.0762 (16) | |
C1 | 0.2461 (7) | 1.0040 (5) | 0.4494 (3) | 0.0464 (9) | |
C2 | 0.2101 (6) | 0.9088 (4) | 0.3469 (3) | 0.0340 (7) | |
C3 | 0.2396 (6) | 0.7571 (4) | 0.3366 (3) | 0.0345 (7) | |
C4 | 0.3174 (8) | 0.7015 (5) | 0.4266 (3) | 0.0485 (10) | |
C5 | 0.6400 (7) | 0.2837 (5) | 0.0812 (3) | 0.0447 (9) | |
H5A | 0.720150 | 0.357762 | 0.064619 | 0.054* | |
H5AB | 0.679124 | 0.190432 | 0.049338 | 0.054* | |
C6 | 0.4254 (10) | 0.2944 (9) | 0.0344 (5) | 0.082 (2) | |
H6A | 0.411122 | 0.298234 | −0.037344 | 0.124* | |
H6B | 0.380116 | 0.380466 | 0.071717 | 0.124* | |
H6C | 0.347336 | 0.211203 | 0.038953 | 0.124* | |
C7 | 0.6058 (7) | 0.4660 (4) | 0.2809 (3) | 0.0395 (8) | |
H7A | 0.462620 | 0.462406 | 0.255927 | 0.047* | |
H7AB | 0.631621 | 0.471097 | 0.355242 | 0.047* | |
C8 | 0.6992 (9) | 0.6007 (5) | 0.2632 (5) | 0.0590 (13) | |
H8A | 0.666860 | 0.599915 | 0.190263 | 0.089* | |
H8B | 0.841292 | 0.604662 | 0.286730 | 0.089* | |
H8C | 0.649334 | 0.683947 | 0.301423 | 0.089* | |
C9 | 0.9574 (6) | 0.3056 (5) | 0.2575 (4) | 0.0480 (10) | |
H9A | 0.999429 | 0.215866 | 0.221420 | 0.058* | |
H9AB | 1.017988 | 0.384155 | 0.235725 | 0.058* | |
C10 | 1.0346 (10) | 0.3230 (8) | 0.3728 (5) | 0.083 (2) | |
H10A | 0.996669 | 0.236863 | 0.393035 | 0.125* | |
H10B | 0.979175 | 0.404187 | 0.409943 | 0.125* | |
H10C | 1.177311 | 0.338997 | 0.389062 | 0.125* | |
C11 | 0.5701 (7) | 0.1561 (4) | 0.2504 (4) | 0.0439 (9) | |
H11A | 0.599751 | 0.168791 | 0.325510 | 0.053* | |
H11B | 0.427286 | 0.158849 | 0.227469 | 0.053* | |
C12 | 0.6282 (8) | 0.0105 (5) | 0.2025 (5) | 0.0608 (14) | |
H12A | 0.610193 | 0.000174 | 0.128577 | 0.091* | |
H12B | 0.546162 | −0.063657 | 0.216209 | 0.091* | |
H12C | 0.765531 | 0.001795 | 0.232005 | 0.091* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Te1 | 0.03133 (11) | 0.02183 (9) | 0.02766 (10) | 0.00372 (7) | 0.00701 (7) | 0.00531 (7) |
Cl1 | 0.0608 (9) | 0.0270 (6) | 0.0644 (10) | 0.0003 (6) | 0.0212 (8) | 0.0000 (6) |
Cl2 | 0.0891 (13) | 0.0414 (8) | 0.0815 (12) | 0.0247 (8) | 0.0449 (11) | 0.0347 (8) |
P1 | 0.0322 (4) | 0.0283 (4) | 0.0333 (4) | 0.0051 (3) | 0.0112 (3) | 0.0064 (3) |
N1 | 0.0407 (16) | 0.0250 (13) | 0.0358 (15) | 0.0058 (11) | 0.0087 (12) | 0.0035 (11) |
N2 | 0.0414 (16) | 0.0273 (13) | 0.0323 (14) | 0.0066 (11) | 0.0086 (12) | 0.0099 (11) |
N3 | 0.100 (4) | 0.067 (3) | 0.041 (2) | 0.019 (3) | 0.004 (2) | −0.008 (2) |
N4 | 0.125 (5) | 0.065 (3) | 0.043 (2) | 0.029 (3) | 0.016 (3) | 0.024 (2) |
C1 | 0.052 (2) | 0.041 (2) | 0.039 (2) | 0.0064 (18) | 0.0028 (18) | 0.0009 (16) |
C2 | 0.0368 (17) | 0.0307 (16) | 0.0314 (16) | 0.0035 (13) | 0.0066 (13) | 0.0010 (13) |
C3 | 0.0404 (18) | 0.0329 (16) | 0.0318 (16) | 0.0064 (14) | 0.0099 (14) | 0.0087 (13) |
C4 | 0.065 (3) | 0.051 (2) | 0.0308 (18) | 0.009 (2) | 0.0108 (18) | 0.0107 (17) |
C5 | 0.048 (2) | 0.053 (2) | 0.0363 (19) | 0.0048 (19) | 0.0132 (17) | 0.0127 (17) |
C6 | 0.076 (4) | 0.098 (5) | 0.057 (3) | 0.018 (4) | −0.021 (3) | 0.014 (3) |
C7 | 0.050 (2) | 0.0304 (16) | 0.044 (2) | 0.0082 (15) | 0.0221 (17) | 0.0083 (15) |
C8 | 0.066 (3) | 0.032 (2) | 0.088 (4) | 0.006 (2) | 0.038 (3) | 0.012 (2) |
C9 | 0.0339 (19) | 0.037 (2) | 0.068 (3) | 0.0059 (15) | 0.0054 (19) | 0.0054 (19) |
C10 | 0.066 (4) | 0.077 (4) | 0.081 (4) | 0.017 (3) | −0.024 (3) | 0.001 (3) |
C11 | 0.052 (2) | 0.0333 (18) | 0.054 (2) | 0.0032 (16) | 0.025 (2) | 0.0120 (17) |
C12 | 0.055 (3) | 0.031 (2) | 0.099 (4) | 0.0029 (18) | 0.032 (3) | 0.007 (2) |
Geometric parameters (Å, º) top
Te1—N2 | 2.020 (3) | C7—C8 | 1.514 (6) |
Te1—N1 | 2.023 (3) | C7—H7A | 0.9800 |
P1—C5 | 1.793 (4) | C7—H7AB | 0.9800 |
P1—C7 | 1.796 (4) | C8—H8A | 0.9700 |
P1—C9 | 1.800 (4) | C8—H8B | 0.9700 |
P1—C11 | 1.807 (4) | C8—H8C | 0.9700 |
N1—C2 | 1.305 (5) | C9—C10 | 1.520 (8) |
N2—C3 | 1.293 (5) | C9—H9A | 0.9800 |
N3—C1 | 1.138 (6) | C9—H9AB | 0.9800 |
N4—C4 | 1.145 (6) | C10—H10A | 0.9700 |
C1—C2 | 1.460 (5) | C10—H10B | 0.9700 |
C2—C3 | 1.457 (5) | C10—H10C | 0.9700 |
C3—C4 | 1.450 (6) | C11—C12 | 1.514 (6) |
C5—C6 | 1.512 (7) | C11—H11A | 0.9800 |
C5—H5A | 0.9800 | C11—H11B | 0.9800 |
C5—H5AB | 0.9800 | C12—H12A | 0.9700 |
C6—H6A | 0.9700 | C12—H12B | 0.9700 |
C6—H6B | 0.9700 | C12—H12C | 0.9700 |
C6—H6C | 0.9700 | | |
| | | |
N2—Te1—N1 | 84.57 (13) | P1—C7—H7AB | 108.8 |
C5—P1—C7 | 110.9 (2) | H7A—C7—H7AB | 107.6 |
C5—P1—C9 | 106.0 (2) | C7—C8—H8A | 109.5 |
C7—P1—C9 | 111.1 (2) | C7—C8—H8B | 109.5 |
C5—P1—C11 | 109.7 (2) | H8A—C8—H8B | 109.5 |
C7—P1—C11 | 107.54 (19) | C7—C8—H8C | 109.5 |
C9—P1—C11 | 111.5 (2) | H8A—C8—H8C | 109.5 |
C2—N1—Te1 | 108.5 (2) | H8B—C8—H8C | 109.5 |
C3—N2—Te1 | 108.7 (2) | C10—C9—P1 | 114.5 (4) |
N3—C1—C2 | 176.8 (6) | C10—C9—H9A | 108.6 |
N1—C2—C3 | 118.8 (3) | P1—C9—H9A | 108.6 |
N1—C2—C1 | 121.4 (4) | C10—C9—H9AB | 108.6 |
C3—C2—C1 | 119.7 (4) | P1—C9—H9AB | 108.6 |
N2—C3—C4 | 120.0 (4) | H9A—C9—H9AB | 107.6 |
N2—C3—C2 | 119.4 (3) | C9—C10—H10A | 109.5 |
C4—C3—C2 | 120.6 (4) | C9—C10—H10B | 109.5 |
N4—C4—C3 | 179.3 (5) | H10A—C10—H10B | 109.5 |
C6—C5—P1 | 114.1 (4) | C9—C10—H10C | 109.5 |
C6—C5—H5A | 108.7 | H10A—C10—H10C | 109.5 |
P1—C5—H5A | 108.7 | H10B—C10—H10C | 109.5 |
C6—C5—H5AB | 108.7 | C12—C11—P1 | 113.9 (3) |
P1—C5—H5AB | 108.7 | C12—C11—H11A | 108.8 |
H5A—C5—H5AB | 107.6 | P1—C11—H11A | 108.8 |
C5—C6—H6A | 109.5 | C12—C11—H11B | 108.8 |
C5—C6—H6B | 109.5 | P1—C11—H11B | 108.8 |
H6A—C6—H6B | 109.5 | H11A—C11—H11B | 107.7 |
C5—C6—H6C | 109.5 | C11—C12—H12A | 109.5 |
H6A—C6—H6C | 109.5 | C11—C12—H12B | 109.5 |
H6B—C6—H6C | 109.5 | H12A—C12—H12B | 109.5 |
C8—C7—P1 | 114.0 (3) | C11—C12—H12C | 109.5 |
C8—C7—H7A | 108.8 | H12A—C12—H12C | 109.5 |
P1—C7—H7A | 108.8 | H12B—C12—H12C | 109.5 |
C8—C7—H7AB | 108.8 | | |
| | | |
Te1—N1—C2—C3 | 2.1 (4) | C11—P1—C5—C6 | 65.2 (5) |
Te1—N1—C2—C1 | −175.9 (3) | C5—P1—C7—C8 | −61.2 (4) |
Te1—N2—C3—C4 | −178.8 (3) | C9—P1—C7—C8 | 56.5 (5) |
Te1—N2—C3—C2 | 1.4 (4) | C11—P1—C7—C8 | 178.8 (4) |
N1—C2—C3—N2 | −2.6 (6) | C5—P1—C9—C10 | 179.5 (4) |
C1—C2—C3—N2 | 175.5 (4) | C7—P1—C9—C10 | 58.9 (5) |
N1—C2—C3—C4 | 177.7 (4) | C11—P1—C9—C10 | −61.1 (5) |
C1—C2—C3—C4 | −4.3 (6) | C5—P1—C11—C12 | 59.0 (5) |
C7—P1—C5—C6 | −53.5 (5) | C7—P1—C11—C12 | 179.7 (4) |
C9—P1—C5—C6 | −174.3 (4) | C9—P1—C11—C12 | −58.2 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···Cl1i | 0.98 | 2.73 | 3.684 (5) | 164 |
C7—H7AB···N4ii | 0.98 | 2.58 | 3.451 (6) | 148 |
C11—H11A···N4ii | 0.98 | 2.60 | 3.460 (7) | 147 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1. |
1,2,5-Selenodiazole-3,4-dicarbonitrile–hydroquinone (1/1) (1a)
top
Crystal data top
2C4N4Se·C6H6O2 | F(000) = 460 |
Mr = 476.19 | Dx = 1.872 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.2634 (16) Å | Cell parameters from 5992 reflections |
b = 7.4089 (19) Å | θ = 3.0–37.6° |
c = 18.320 (5) Å | µ = 4.41 mm−1 |
β = 96.420 (5)° | T = 203 K |
V = 844.8 (4) Å3 | Plate, orange |
Z = 2 | 0.55 × 0.49 × 0.09 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3289 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ω and πhi scans | θmax = 38.1°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2010) | h = −10→10 |
Tmin = 0.478, Tmax = 0.747 | k = −12→12 |
17649 measured reflections | l = −31→31 |
4607 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0302P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.073 | (Δ/σ)max = 0.001 |
S = 1.00 | Δρmax = 0.63 e Å−3 |
4607 reflections | Δρmin = −0.55 e Å−3 |
120 parameters | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0216 (11) |
Primary atom site location: structure-invariant direct methods | |
Special details top
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. none |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Se1 | 0.72849 (2) | 0.36938 (2) | 0.97332 (2) | 0.02089 (5) | |
O1 | 0.38261 (18) | 0.32324 (16) | 0.54309 (6) | 0.0253 (2) | |
H1 | 0.410146 | 0.326207 | 0.588459 | 0.038* | |
N1 | 0.9199 (2) | 0.48058 (17) | 0.92321 (6) | 0.0212 (2) | |
N2 | 1.0510 (3) | 0.6182 (2) | 0.75384 (9) | 0.0459 (5) | |
N3 | 0.5560 (2) | 0.31610 (19) | 0.89180 (7) | 0.0250 (3) | |
N4 | 0.4783 (3) | 0.3335 (3) | 0.70232 (9) | 0.0428 (4) | |
C1 | 0.9651 (3) | 0.5513 (2) | 0.79843 (8) | 0.0289 (3) | |
C2 | 0.8484 (2) | 0.47000 (19) | 0.85316 (7) | 0.0203 (3) | |
C3 | 0.6477 (2) | 0.3788 (2) | 0.83607 (8) | 0.0217 (3) | |
C4 | 0.5494 (3) | 0.3530 (2) | 0.76190 (9) | 0.0293 (3) | |
C5 | 0.1915 (2) | 0.41095 (19) | 0.52294 (8) | 0.0189 (2) | |
C6 | 0.1351 (2) | 0.44688 (19) | 0.44862 (7) | 0.0198 (3) | |
H6 | 0.226185 | 0.410757 | 0.413872 | 0.024* | |
C7 | −0.0553 (2) | 0.53587 (19) | 0.42603 (7) | 0.0204 (3) | |
H7 | −0.092749 | 0.560488 | 0.375902 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Se1 | 0.02157 (8) | 0.02412 (8) | 0.01721 (7) | −0.00006 (6) | 0.00320 (5) | 0.00112 (5) |
O1 | 0.0211 (5) | 0.0326 (6) | 0.0213 (5) | 0.0056 (4) | −0.0022 (4) | −0.0012 (4) |
N1 | 0.0215 (6) | 0.0228 (6) | 0.0195 (5) | −0.0017 (5) | 0.0027 (4) | −0.0020 (4) |
N2 | 0.0533 (11) | 0.0546 (11) | 0.0321 (8) | −0.0183 (9) | 0.0149 (8) | −0.0007 (7) |
N3 | 0.0206 (6) | 0.0314 (6) | 0.0226 (6) | −0.0034 (5) | 0.0011 (5) | 0.0019 (5) |
N4 | 0.0370 (9) | 0.0612 (11) | 0.0279 (7) | 0.0035 (8) | −0.0064 (7) | −0.0023 (7) |
C1 | 0.0309 (8) | 0.0328 (8) | 0.0237 (7) | −0.0070 (7) | 0.0064 (6) | −0.0021 (6) |
C2 | 0.0212 (6) | 0.0216 (6) | 0.0185 (6) | 0.0000 (5) | 0.0044 (5) | −0.0003 (5) |
C3 | 0.0196 (6) | 0.0259 (7) | 0.0191 (6) | 0.0011 (6) | 0.0000 (5) | 0.0002 (5) |
C4 | 0.0249 (8) | 0.0369 (9) | 0.0251 (7) | 0.0006 (7) | −0.0010 (6) | 0.0020 (6) |
C5 | 0.0177 (6) | 0.0183 (6) | 0.0200 (6) | −0.0004 (5) | −0.0003 (5) | −0.0010 (5) |
C6 | 0.0197 (6) | 0.0229 (7) | 0.0170 (6) | −0.0008 (5) | 0.0034 (5) | −0.0025 (5) |
C7 | 0.0231 (7) | 0.0224 (6) | 0.0154 (6) | −0.0001 (5) | 0.0006 (5) | −0.0013 (5) |
Geometric parameters (Å, º) top
Se1—N3 | 1.7869 (13) | C1—C2 | 1.437 (2) |
Se1—N1 | 1.7901 (13) | C2—C3 | 1.431 (2) |
O1—C5 | 1.3760 (19) | C3—C4 | 1.440 (2) |
O1—H1 | 0.8300 | C5—C7i | 1.391 (2) |
N1—C2 | 1.3134 (18) | C5—C6 | 1.3934 (19) |
N2—C1 | 1.141 (2) | C6—C7 | 1.385 (2) |
N3—C3 | 1.311 (2) | C6—H6 | 0.9400 |
N4—C4 | 1.141 (2) | C7—H7 | 0.9400 |
| | | |
N3—Se1—N1 | 92.87 (6) | N4—C4—C3 | 177.64 (19) |
C5—O1—H1 | 109.5 | O1—C5—C7i | 122.27 (13) |
C2—N1—Se1 | 107.40 (10) | O1—C5—C6 | 118.04 (13) |
C3—N3—Se1 | 107.20 (10) | C7i—C5—C6 | 119.68 (13) |
N2—C1—C2 | 177.6 (2) | C7—C6—C5 | 119.90 (13) |
N1—C2—C3 | 115.92 (13) | C7—C6—H6 | 120.0 |
N1—C2—C1 | 120.83 (14) | C5—C6—H6 | 120.0 |
C3—C2—C1 | 123.23 (13) | C6—C7—C5i | 120.42 (12) |
N3—C3—C2 | 116.60 (13) | C6—C7—H7 | 119.8 |
N3—C3—C4 | 120.63 (14) | C5i—C7—H7 | 119.8 |
C2—C3—C4 | 122.77 (14) | | |
| | | |
N3—Se1—N1—C2 | −0.58 (11) | C1—C2—C3—N3 | −177.88 (15) |
N1—Se1—N3—C3 | 0.71 (11) | N1—C2—C3—C4 | −178.91 (14) |
Se1—N1—C2—C3 | 0.32 (16) | C1—C2—C3—C4 | 3.0 (2) |
Se1—N1—C2—C1 | 178.50 (12) | O1—C5—C6—C7 | −179.61 (13) |
Se1—N3—C3—C2 | −0.67 (17) | C7i—C5—C6—C7 | 0.3 (2) |
Se1—N3—C3—C4 | 178.50 (12) | C5—C6—C7—C5i | −0.3 (2) |
N1—C2—C3—N3 | 0.2 (2) | | |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N4 | 0.83 | 2.08 | 2.913 (2) | 180 |
Chalcogen bond geometriesa topCocrystal | Ch···X distance (Å) | N—Ch···X angle (°) | Nc |
1a | 2.997 (1) (X = O) | 174.41 (5) | 0.88 |
1a | 2.957 (1) (X = N) | 162.97 (5) | 0.86 |
2b | 2.9664 (1) (X = Cl1) | 164.87 (5) | 0.77 |
2b | 3.0842 (1) (X = Cl2) | 171.04 (5) | 0.80 |
2c | 2.6733 (6) (X = Cl) | 168.08 (5) | 0.69 |
2c | 3.959 (X = Ph) | 159.1 | 0.87 |
(a) Van der Waals radii (Å) used: Te 2.06, Se 1.90, Cl- 1.81,
O 1.52, and N 1.55 (Bondi, 1964; Shannon, 1976). |
Selenium-77 and tellurium-125 chemical shift tensor dataa topCompound | Nucleus | δiso (ppm) | Ω (ppm) | κ | δ11 (ppm) | δ22 (ppm) | δ33 (ppm) |
1b,c(site 1) | 77Se | 1592.2(0.1) | 472 (5) | 0.05(0.01) | 1824 (4) | 1600 (2) | 1352 (3) |
1b,c(site 2) | 77Se | 1548.7(0.1) | 456 (3) | -0.47(0.01) | 1812 (3) | 1477 (1) | 1356 (2) |
1a | 77Se | 1601 (2) | 466 (10) | -0.11(0.02) | 1849 (4) | 1582 (3) | 1366 (3) |
2b | 125Te | 2332.8(0.1) | 1268 (3) | 0.49(0.01) | 2863 (5) | 2540 (3) | 1595 (4) |
2b | 125Te | 2385 (1) | 955 (10) | 0.72(0.02) | 2746 (3) | 2614 (2) | 1791 (2) |
2c | 125Te | 2160 (1) | 966 (10) | 0.23(0.02) | 2606 (4) | 2234 (3) | 1640 (3) |
Notes: (a) errors given are estimated from independently fitting data acquired
at 9.4 and 11.75 T using an iterative Herzfeld–Berger routine. (b) Data from
Kumar et al. (2020a). (c) Two crystallographic sites. |
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