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The title compound, C
33H
28N
16S
4, prepared by the divergent method, presents a core unit for further synthesis of tetrazole-containing dendrimers. The central C atom lies on a crystallographic twofold rotation axis. π–π Interactions and weak non-classical C—H
N hydrogen bonds are responsible for the formation of layers parallel to the
bc plane, with van der Waals interactions between them.
Supporting information
CCDC reference: 640250
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.123
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.86 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8A
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.
Tetrakis[(1-phenyltetrazol-5-yl)sulfanylmethyl]methane
top
Crystal data top
C33H28N16S4 | F(000) = 804 |
Mr = 776.95 | Dx = 1.432 Mg m−3 |
Monoclinic, P2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yc | Cell parameters from 25 reflections |
a = 16.213 (4) Å | θ = 10.1–15.4° |
b = 7.1194 (14) Å | µ = 0.32 mm−1 |
c = 17.748 (4) Å | T = 294 K |
β = 118.418 (17)° | Prism, colourless |
V = 1801.7 (8) Å3 | 0.36 × 0.22 × 0.12 mm |
Z = 2 | |
Data collection top
Nicolet R3m four-circle diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 27.6°, θmin = 1.4° |
Graphite monochromator | h = 0→21 |
ω/2θ scans | k = −9→0 |
4358 measured reflections | l = −23→20 |
4167 independent reflections | 3 standard reflections every 100 reflections |
2865 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0637P)2 + 0.2533P] where P = (Fo2 + 2Fc2)/3 |
4167 reflections | (Δ/σ)max < 0.001 |
240 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Special details top
Experimental. 1H NMR (400 MHz, DMSO-d6, δ, p.p.m.): 4.00 (s, 8H, CH2), 7.70 (s, 20H,
aryl); IR (KBr, cm-1) ν: 979, 1013, 1059, 1075, 1092, 1239, 1276, 1382,
1395, 1417, 1462, 1500, 1596, 2918, 2996, 3070, 3103. |
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. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.5000 | 0.2100 (4) | 0.7500 | 0.0338 (5) | |
C2A | 0.56264 (13) | 0.0889 (3) | 0.82815 (12) | 0.0383 (4) | |
H2A | 0.5224 | 0.0208 | 0.8452 | 0.046* | |
H2B | 0.6012 | 0.1726 | 0.8749 | 0.046* | |
S1A | 0.63934 (3) | −0.07919 (8) | 0.81599 (3) | 0.04381 (15) | |
N1A | 0.82231 (11) | −0.0072 (3) | 0.86038 (11) | 0.0453 (4) | |
N2A | 0.88852 (13) | 0.1267 (3) | 0.90252 (14) | 0.0642 (6) | |
N3A | 0.84815 (15) | 0.2584 (3) | 0.92251 (16) | 0.0691 (6) | |
N4A | 0.75638 (13) | 0.2174 (3) | 0.89529 (13) | 0.0554 (5) | |
C5A | 0.74181 (13) | 0.0517 (3) | 0.85801 (12) | 0.0414 (5) | |
C6A | 0.84486 (14) | −0.1711 (3) | 0.82790 (14) | 0.0454 (5) | |
C7A | 0.93147 (17) | −0.2524 (4) | 0.87515 (18) | 0.0713 (8) | |
H7A | 0.9738 | −0.2045 | 0.9285 | 0.086* | |
C8A | 0.9540 (2) | −0.4062 (5) | 0.8417 (2) | 0.0968 (11) | |
H8A | 1.0125 | −0.4624 | 0.8725 | 0.116* | |
C9A | 0.8907 (2) | −0.4776 (5) | 0.7630 (3) | 0.0887 (10) | |
H9A | 0.9065 | −0.5817 | 0.7409 | 0.106* | |
C10A | 0.8053 (2) | −0.3962 (4) | 0.71784 (19) | 0.0689 (7) | |
H10A | 0.7627 | −0.4453 | 0.6649 | 0.083* | |
C11A | 0.78148 (16) | −0.2422 (4) | 0.74967 (15) | 0.0537 (6) | |
H11A | 0.7229 | −0.1864 | 0.7185 | 0.064* | |
C2B | 0.55503 (14) | 0.3464 (3) | 0.72216 (13) | 0.0417 (5) | |
H2C | 0.5961 | 0.4206 | 0.7718 | 0.050* | |
H2D | 0.5101 | 0.4323 | 0.6804 | 0.050* | |
S1B | 0.62580 (3) | 0.24983 (10) | 0.67687 (3) | 0.05162 (18) | |
N1B | 0.58620 (11) | 0.2469 (2) | 0.51157 (10) | 0.0398 (4) | |
N2B | 0.51303 (13) | 0.2617 (3) | 0.43113 (11) | 0.0491 (4) | |
N3B | 0.43934 (12) | 0.2861 (3) | 0.44001 (11) | 0.0499 (4) | |
N4B | 0.46059 (11) | 0.2882 (3) | 0.52414 (11) | 0.0455 (4) | |
C5B | 0.55217 (13) | 0.2630 (3) | 0.56752 (13) | 0.0398 (4) | |
C6B | 0.68126 (14) | 0.2261 (3) | 0.52770 (12) | 0.0406 (4) | |
C7B | 0.72932 (16) | 0.0654 (3) | 0.56659 (16) | 0.0539 (6) | |
H7B | 0.7008 | −0.0296 | 0.5820 | 0.065* | |
C8B | 0.82150 (17) | 0.0476 (4) | 0.58248 (19) | 0.0659 (7) | |
H8B | 0.8559 | −0.0588 | 0.6101 | 0.079* | |
C9B | 0.86170 (17) | 0.1861 (4) | 0.55768 (17) | 0.0634 (7) | |
H9B | 0.9234 | 0.1732 | 0.5685 | 0.076* | |
C10B | 0.81193 (17) | 0.3443 (4) | 0.51697 (16) | 0.0587 (6) | |
H10B | 0.8397 | 0.4365 | 0.4994 | 0.070* | |
C11B | 0.72088 (15) | 0.3670 (3) | 0.50210 (14) | 0.0484 (5) | |
H11B | 0.6870 | 0.4746 | 0.4755 | 0.058* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0309 (12) | 0.0425 (15) | 0.0311 (12) | 0.000 | 0.0173 (10) | 0.000 |
C2A | 0.0340 (9) | 0.0499 (12) | 0.0366 (9) | 0.0039 (9) | 0.0215 (8) | 0.0038 (9) |
S1A | 0.0355 (3) | 0.0472 (3) | 0.0513 (3) | 0.0038 (2) | 0.0228 (2) | 0.0013 (2) |
N1A | 0.0308 (8) | 0.0576 (11) | 0.0447 (9) | −0.0001 (8) | 0.0158 (7) | −0.0056 (8) |
N2A | 0.0384 (10) | 0.0734 (15) | 0.0748 (14) | −0.0103 (10) | 0.0221 (10) | −0.0195 (12) |
N3A | 0.0473 (11) | 0.0725 (15) | 0.0834 (15) | −0.0098 (11) | 0.0276 (11) | −0.0251 (12) |
N4A | 0.0451 (10) | 0.0592 (12) | 0.0609 (12) | −0.0010 (9) | 0.0244 (9) | −0.0125 (10) |
C5A | 0.0330 (9) | 0.0520 (12) | 0.0390 (10) | 0.0047 (9) | 0.0168 (8) | 0.0005 (9) |
C6A | 0.0358 (10) | 0.0550 (13) | 0.0487 (11) | 0.0037 (9) | 0.0228 (9) | 0.0002 (10) |
C7A | 0.0428 (12) | 0.094 (2) | 0.0646 (16) | 0.0173 (13) | 0.0153 (12) | −0.0066 (15) |
C8A | 0.0642 (18) | 0.104 (3) | 0.113 (3) | 0.0412 (18) | 0.0347 (19) | −0.003 (2) |
C9A | 0.095 (2) | 0.072 (2) | 0.117 (3) | 0.0134 (18) | 0.065 (2) | −0.0182 (19) |
C10A | 0.0646 (16) | 0.0766 (19) | 0.0774 (18) | −0.0097 (14) | 0.0435 (14) | −0.0215 (15) |
C11A | 0.0444 (12) | 0.0679 (16) | 0.0515 (12) | 0.0014 (11) | 0.0251 (10) | −0.0064 (11) |
C2B | 0.0410 (10) | 0.0493 (12) | 0.0382 (10) | −0.0067 (9) | 0.0215 (8) | −0.0010 (9) |
S1B | 0.0343 (3) | 0.0874 (5) | 0.0381 (3) | 0.0011 (3) | 0.0211 (2) | 0.0100 (3) |
N1B | 0.0372 (8) | 0.0483 (10) | 0.0358 (8) | −0.0010 (7) | 0.0189 (7) | −0.0001 (7) |
N2B | 0.0479 (10) | 0.0607 (12) | 0.0359 (9) | 0.0002 (9) | 0.0178 (8) | −0.0032 (8) |
N3B | 0.0413 (9) | 0.0603 (12) | 0.0429 (9) | −0.0017 (9) | 0.0158 (8) | −0.0009 (9) |
N4B | 0.0365 (8) | 0.0584 (11) | 0.0434 (9) | −0.0022 (8) | 0.0204 (7) | 0.0052 (8) |
C5B | 0.0364 (10) | 0.0467 (11) | 0.0404 (10) | −0.0026 (9) | 0.0215 (8) | 0.0035 (9) |
C6B | 0.0398 (10) | 0.0502 (12) | 0.0367 (10) | −0.0024 (9) | 0.0222 (8) | −0.0046 (9) |
C7B | 0.0495 (12) | 0.0553 (14) | 0.0658 (14) | 0.0020 (11) | 0.0348 (11) | 0.0076 (12) |
C8B | 0.0522 (14) | 0.0694 (17) | 0.0808 (17) | 0.0119 (13) | 0.0354 (13) | 0.0076 (14) |
C9B | 0.0449 (12) | 0.0847 (19) | 0.0690 (16) | −0.0059 (13) | 0.0340 (12) | −0.0087 (14) |
C10B | 0.0531 (13) | 0.0697 (16) | 0.0619 (14) | −0.0177 (13) | 0.0344 (11) | −0.0052 (13) |
C11B | 0.0493 (12) | 0.0527 (13) | 0.0459 (11) | −0.0069 (10) | 0.0249 (10) | −0.0016 (10) |
Geometric parameters (Å, º) top
C1—C2A | 1.535 (2) | C10A—H10A | 0.9300 |
C1—C2Ai | 1.535 (2) | C11A—H11A | 0.9300 |
C1—C2B | 1.550 (3) | C2B—S1B | 1.820 (2) |
C1—C2Bi | 1.550 (3) | C2B—H2C | 0.9700 |
C2A—S1A | 1.8115 (19) | C2B—H2D | 0.9700 |
C2A—H2A | 0.9700 | S1B—C5B | 1.731 (2) |
C2A—H2B | 0.9700 | N1B—C5B | 1.351 (2) |
S1A—C5A | 1.733 (2) | N1B—N2B | 1.358 (2) |
N1A—C5A | 1.352 (2) | N1B—C6B | 1.435 (2) |
N1A—N2A | 1.363 (3) | N2B—N3B | 1.289 (3) |
N1A—C6A | 1.424 (3) | N3B—N4B | 1.363 (3) |
N2A—N3A | 1.286 (3) | N4B—C5B | 1.320 (2) |
N3A—N4A | 1.359 (3) | C6B—C7B | 1.371 (3) |
N4A—C5A | 1.318 (3) | C6B—C11B | 1.379 (3) |
C6A—C11A | 1.372 (3) | C7B—C8B | 1.389 (3) |
C6A—C7A | 1.374 (3) | C7B—H7B | 0.9300 |
C7A—C8A | 1.375 (4) | C8B—C9B | 1.365 (4) |
C7A—H7A | 0.9300 | C8B—H8B | 0.9300 |
C8A—C9A | 1.378 (5) | C9B—C10B | 1.374 (4) |
C8A—H8A | 0.9300 | C9B—H9B | 0.9300 |
C9A—C10A | 1.356 (4) | C10B—C11B | 1.380 (3) |
C9A—H9A | 0.9300 | C10B—H10B | 0.9300 |
C10A—C11A | 1.371 (4) | C11B—H11B | 0.9300 |
| | | |
C2A—C1—C2Ai | 111.7 (2) | C10A—C11A—C6A | 119.3 (2) |
C2A—C1—C2B | 113.95 (11) | C10A—C11A—H11A | 120.3 |
C2Ai—C1—C2B | 107.30 (10) | C6A—C11A—H11A | 120.3 |
C2A—C1—C2Bi | 107.30 (10) | C1—C2B—S1B | 118.92 (16) |
C2Ai—C1—C2Bi | 113.96 (11) | C1—C2B—H2C | 107.6 |
C2B—C1—C2Bi | 102.4 (2) | S1B—C2B—H2C | 107.6 |
C1—C2A—S1A | 117.38 (12) | C1—C2B—H2D | 107.6 |
C1—C2A—H2A | 108.0 | S1B—C2B—H2D | 107.6 |
S1A—C2A—H2A | 108.0 | H2C—C2B—H2D | 107.0 |
C1—C2A—H2B | 108.0 | C5B—S1B—C2B | 103.38 (10) |
S1A—C2A—H2B | 108.0 | C5B—N1B—N2B | 107.95 (16) |
H2A—C2A—H2B | 107.2 | C5B—N1B—C6B | 129.62 (17) |
C5A—S1A—C2A | 99.51 (10) | N2B—N1B—C6B | 122.38 (16) |
C5A—N1A—N2A | 107.25 (18) | N3B—N2B—N1B | 106.18 (16) |
C5A—N1A—C6A | 132.18 (18) | N2B—N3B—N4B | 111.69 (16) |
N2A—N1A—C6A | 120.57 (17) | C5B—N4B—N3B | 105.38 (16) |
N3A—N2A—N1A | 106.87 (18) | N4B—C5B—N1B | 108.81 (17) |
N2A—N3A—N4A | 111.1 (2) | N4B—C5B—S1B | 130.22 (15) |
C5A—N4A—N3A | 105.96 (18) | N1B—C5B—S1B | 120.97 (15) |
N4A—C5A—N1A | 108.80 (18) | C7B—C6B—C11B | 122.0 (2) |
N4A—C5A—S1A | 127.10 (16) | C7B—C6B—N1B | 119.04 (18) |
N1A—C5A—S1A | 124.04 (17) | C11B—C6B—N1B | 118.92 (19) |
C11A—C6A—C7A | 121.2 (2) | C6B—C7B—C8B | 118.5 (2) |
C11A—C6A—N1A | 119.93 (19) | C6B—C7B—H7B | 120.8 |
C7A—C6A—N1A | 118.9 (2) | C8B—C7B—H7B | 120.8 |
C6A—C7A—C8A | 118.4 (3) | C9B—C8B—C7B | 120.1 (3) |
C6A—C7A—H7A | 120.8 | C9B—C8B—H8B | 119.9 |
C8A—C7A—H7A | 120.8 | C7B—C8B—H8B | 119.9 |
C7A—C8A—C9A | 120.6 (3) | C8B—C9B—C10B | 120.7 (2) |
C7A—C8A—H8A | 119.7 | C8B—C9B—H9B | 119.6 |
C9A—C8A—H8A | 119.7 | C10B—C9B—H9B | 119.6 |
C10A—C9A—C8A | 120.0 (3) | C9B—C10B—C11B | 120.2 (2) |
C10A—C9A—H9A | 120.0 | C9B—C10B—H10B | 119.9 |
C8A—C9A—H9A | 120.0 | C11B—C10B—H10B | 119.9 |
C9A—C10A—C11A | 120.5 (3) | C6B—C11B—C10B | 118.4 (2) |
C9A—C10A—H10A | 119.8 | C6B—C11B—H11B | 120.8 |
C11A—C10A—H10A | 119.8 | C10B—C11B—H11B | 120.8 |
| | | |
C2Ai—C1—C2A—S1A | 56.77 (11) | C2A—C1—C2B—S1B | 68.41 (19) |
C2B—C1—C2A—S1A | −65.0 (2) | C2Ai—C1—C2B—S1B | −55.80 (18) |
C2Bi—C1—C2A—S1A | −177.66 (14) | C2Bi—C1—C2B—S1B | −176.06 (18) |
C1—C2A—S1A—C5A | 96.39 (16) | C1—C2B—S1B—C5B | 95.74 (14) |
C5A—N1A—N2A—N3A | −0.9 (3) | C5B—N1B—N2B—N3B | 0.2 (2) |
C6A—N1A—N2A—N3A | 178.6 (2) | C6B—N1B—N2B—N3B | −177.42 (19) |
N1A—N2A—N3A—N4A | 0.2 (3) | N1B—N2B—N3B—N4B | 0.0 (2) |
N2A—N3A—N4A—C5A | 0.7 (3) | N2B—N3B—N4B—C5B | −0.2 (2) |
N3A—N4A—C5A—N1A | −1.3 (3) | N3B—N4B—C5B—N1B | 0.3 (2) |
N3A—N4A—C5A—S1A | 176.21 (18) | N3B—N4B—C5B—S1B | −179.69 (17) |
N2A—N1A—C5A—N4A | 1.4 (2) | N2B—N1B—C5B—N4B | −0.3 (2) |
C6A—N1A—C5A—N4A | −178.1 (2) | C6B—N1B—C5B—N4B | 177.1 (2) |
N2A—N1A—C5A—S1A | −176.18 (16) | N2B—N1B—C5B—S1B | 179.68 (14) |
C6A—N1A—C5A—S1A | 4.4 (3) | C6B—N1B—C5B—S1B | −2.9 (3) |
C2A—S1A—C5A—N4A | 6.2 (2) | C2B—S1B—C5B—N4B | −16.1 (2) |
C2A—S1A—C5A—N1A | −176.63 (17) | C2B—S1B—C5B—N1B | 163.90 (17) |
C5A—N1A—C6A—C11A | 39.0 (3) | C5B—N1B—C6B—C7B | 65.8 (3) |
N2A—N1A—C6A—C11A | −140.4 (2) | N2B—N1B—C6B—C7B | −117.1 (2) |
C5A—N1A—C6A—C7A | −142.7 (3) | C5B—N1B—C6B—C11B | −115.4 (2) |
N2A—N1A—C6A—C7A | 37.9 (3) | N2B—N1B—C6B—C11B | 61.7 (3) |
C11A—C6A—C7A—C8A | 0.8 (4) | C11B—C6B—C7B—C8B | 1.8 (3) |
N1A—C6A—C7A—C8A | −177.5 (3) | N1B—C6B—C7B—C8B | −179.5 (2) |
C6A—C7A—C8A—C9A | −0.6 (5) | C6B—C7B—C8B—C9B | −1.6 (4) |
C7A—C8A—C9A—C10A | 0.0 (6) | C7B—C8B—C9B—C10B | 0.1 (4) |
C8A—C9A—C10A—C11A | 0.3 (5) | C8B—C9B—C10B—C11B | 1.3 (4) |
C9A—C10A—C11A—C6A | −0.1 (4) | C7B—C6B—C11B—C10B | −0.4 (3) |
C7A—C6A—C11A—C10A | −0.5 (4) | N1B—C6B—C11B—C10B | −179.18 (19) |
N1A—C6A—C11A—C10A | 177.8 (2) | C9B—C10B—C11B—C6B | −1.1 (4) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2A—H2A···N2Bii | 0.97 | 2.57 | 3.409 (3) | 145 |
C10B—H10B···N3Aiii | 0.93 | 2.60 | 3.478 (4) | 157 |
Symmetry codes: (ii) x, −y, z+1/2; (iii) x, −y+1, z−1/2. |
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