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The title compound, C33H28N16S4, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004400/bg2022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004400/bg2022Isup2.hkl
Contains datablock I

CCDC reference: 640250

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.123
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

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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

Computing details top

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
C33H28N16S4F(000) = 804
Mr = 776.95Dx = 1.432 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 25 reflections
a = 16.213 (4) Åθ = 10.1–15.4°
b = 7.1194 (14) ŵ = 0.32 mm1
c = 17.748 (4) ÅT = 294 K
β = 118.418 (17)°Prism, colourless
V = 1801.7 (8) Å30.36 × 0.22 × 0.12 mm
Z = 2
Data collection top
Nicolet R3m four-circle
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 27.6°, θmin = 1.4°
Graphite monochromatorh = 021
ω/2θ scansk = 90
4358 measured reflectionsl = 2320
4167 independent reflections3 standard reflections every 100 reflections
2865 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.37 e Å3
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
xyzUiso*/Ueq
C10.50000.2100 (4)0.75000.0338 (5)
C2A0.56264 (13)0.0889 (3)0.82815 (12)0.0383 (4)
H2A0.52240.02080.84520.046*
H2B0.60120.17260.87490.046*
S1A0.63934 (3)0.07919 (8)0.81599 (3)0.04381 (15)
N1A0.82231 (11)0.0072 (3)0.86038 (11)0.0453 (4)
N2A0.88852 (13)0.1267 (3)0.90252 (14)0.0642 (6)
N3A0.84815 (15)0.2584 (3)0.92251 (16)0.0691 (6)
N4A0.75638 (13)0.2174 (3)0.89529 (13)0.0554 (5)
C5A0.74181 (13)0.0517 (3)0.85801 (12)0.0414 (5)
C6A0.84486 (14)0.1711 (3)0.82790 (14)0.0454 (5)
C7A0.93147 (17)0.2524 (4)0.87515 (18)0.0713 (8)
H7A0.97380.20450.92850.086*
C8A0.9540 (2)0.4062 (5)0.8417 (2)0.0968 (11)
H8A1.01250.46240.87250.116*
C9A0.8907 (2)0.4776 (5)0.7630 (3)0.0887 (10)
H9A0.90650.58170.74090.106*
C10A0.8053 (2)0.3962 (4)0.71784 (19)0.0689 (7)
H10A0.76270.44530.66490.083*
C11A0.78148 (16)0.2422 (4)0.74967 (15)0.0537 (6)
H11A0.72290.18640.71850.064*
C2B0.55503 (14)0.3464 (3)0.72216 (13)0.0417 (5)
H2C0.59610.42060.77180.050*
H2D0.51010.43230.68040.050*
S1B0.62580 (3)0.24983 (10)0.67687 (3)0.05162 (18)
N1B0.58620 (11)0.2469 (2)0.51157 (10)0.0398 (4)
N2B0.51303 (13)0.2617 (3)0.43113 (11)0.0491 (4)
N3B0.43934 (12)0.2861 (3)0.44001 (11)0.0499 (4)
N4B0.46059 (11)0.2882 (3)0.52414 (11)0.0455 (4)
C5B0.55217 (13)0.2630 (3)0.56752 (13)0.0398 (4)
C6B0.68126 (14)0.2261 (3)0.52770 (12)0.0406 (4)
C7B0.72932 (16)0.0654 (3)0.56659 (16)0.0539 (6)
H7B0.70080.02960.58200.065*
C8B0.82150 (17)0.0476 (4)0.58248 (19)0.0659 (7)
H8B0.85590.05880.61010.079*
C9B0.86170 (17)0.1861 (4)0.55768 (17)0.0634 (7)
H9B0.92340.17320.56850.076*
C10B0.81193 (17)0.3443 (4)0.51697 (16)0.0587 (6)
H10B0.83970.43650.49940.070*
C11B0.72088 (15)0.3670 (3)0.50210 (14)0.0484 (5)
H11B0.68700.47460.47550.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0309 (12)0.0425 (15)0.0311 (12)0.0000.0173 (10)0.000
C2A0.0340 (9)0.0499 (12)0.0366 (9)0.0039 (9)0.0215 (8)0.0038 (9)
S1A0.0355 (3)0.0472 (3)0.0513 (3)0.0038 (2)0.0228 (2)0.0013 (2)
N1A0.0308 (8)0.0576 (11)0.0447 (9)0.0001 (8)0.0158 (7)0.0056 (8)
N2A0.0384 (10)0.0734 (15)0.0748 (14)0.0103 (10)0.0221 (10)0.0195 (12)
N3A0.0473 (11)0.0725 (15)0.0834 (15)0.0098 (11)0.0276 (11)0.0251 (12)
N4A0.0451 (10)0.0592 (12)0.0609 (12)0.0010 (9)0.0244 (9)0.0125 (10)
C5A0.0330 (9)0.0520 (12)0.0390 (10)0.0047 (9)0.0168 (8)0.0005 (9)
C6A0.0358 (10)0.0550 (13)0.0487 (11)0.0037 (9)0.0228 (9)0.0002 (10)
C7A0.0428 (12)0.094 (2)0.0646 (16)0.0173 (13)0.0153 (12)0.0066 (15)
C8A0.0642 (18)0.104 (3)0.113 (3)0.0412 (18)0.0347 (19)0.003 (2)
C9A0.095 (2)0.072 (2)0.117 (3)0.0134 (18)0.065 (2)0.0182 (19)
C10A0.0646 (16)0.0766 (19)0.0774 (18)0.0097 (14)0.0435 (14)0.0215 (15)
C11A0.0444 (12)0.0679 (16)0.0515 (12)0.0014 (11)0.0251 (10)0.0064 (11)
C2B0.0410 (10)0.0493 (12)0.0382 (10)0.0067 (9)0.0215 (8)0.0010 (9)
S1B0.0343 (3)0.0874 (5)0.0381 (3)0.0011 (3)0.0211 (2)0.0100 (3)
N1B0.0372 (8)0.0483 (10)0.0358 (8)0.0010 (7)0.0189 (7)0.0001 (7)
N2B0.0479 (10)0.0607 (12)0.0359 (9)0.0002 (9)0.0178 (8)0.0032 (8)
N3B0.0413 (9)0.0603 (12)0.0429 (9)0.0017 (9)0.0158 (8)0.0009 (9)
N4B0.0365 (8)0.0584 (11)0.0434 (9)0.0022 (8)0.0204 (7)0.0052 (8)
C5B0.0364 (10)0.0467 (11)0.0404 (10)0.0026 (9)0.0215 (8)0.0035 (9)
C6B0.0398 (10)0.0502 (12)0.0367 (10)0.0024 (9)0.0222 (8)0.0046 (9)
C7B0.0495 (12)0.0553 (14)0.0658 (14)0.0020 (11)0.0348 (11)0.0076 (12)
C8B0.0522 (14)0.0694 (17)0.0808 (17)0.0119 (13)0.0354 (13)0.0076 (14)
C9B0.0449 (12)0.0847 (19)0.0690 (16)0.0059 (13)0.0340 (12)0.0087 (14)
C10B0.0531 (13)0.0697 (16)0.0619 (14)0.0177 (13)0.0344 (11)0.0052 (13)
C11B0.0493 (12)0.0527 (13)0.0459 (11)0.0069 (10)0.0249 (10)0.0016 (10)
Geometric parameters (Å, º) top
C1—C2A1.535 (2)C10A—H10A0.9300
C1—C2Ai1.535 (2)C11A—H11A0.9300
C1—C2B1.550 (3)C2B—S1B1.820 (2)
C1—C2Bi1.550 (3)C2B—H2C0.9700
C2A—S1A1.8115 (19)C2B—H2D0.9700
C2A—H2A0.9700S1B—C5B1.731 (2)
C2A—H2B0.9700N1B—C5B1.351 (2)
S1A—C5A1.733 (2)N1B—N2B1.358 (2)
N1A—C5A1.352 (2)N1B—C6B1.435 (2)
N1A—N2A1.363 (3)N2B—N3B1.289 (3)
N1A—C6A1.424 (3)N3B—N4B1.363 (3)
N2A—N3A1.286 (3)N4B—C5B1.320 (2)
N3A—N4A1.359 (3)C6B—C7B1.371 (3)
N4A—C5A1.318 (3)C6B—C11B1.379 (3)
C6A—C11A1.372 (3)C7B—C8B1.389 (3)
C6A—C7A1.374 (3)C7B—H7B0.9300
C7A—C8A1.375 (4)C8B—C9B1.365 (4)
C7A—H7A0.9300C8B—H8B0.9300
C8A—C9A1.378 (5)C9B—C10B1.374 (4)
C8A—H8A0.9300C9B—H9B0.9300
C9A—C10A1.356 (4)C10B—C11B1.380 (3)
C9A—H9A0.9300C10B—H10B0.9300
C10A—C11A1.371 (4)C11B—H11B0.9300
C2A—C1—C2Ai111.7 (2)C10A—C11A—C6A119.3 (2)
C2A—C1—C2B113.95 (11)C10A—C11A—H11A120.3
C2Ai—C1—C2B107.30 (10)C6A—C11A—H11A120.3
C2A—C1—C2Bi107.30 (10)C1—C2B—S1B118.92 (16)
C2Ai—C1—C2Bi113.96 (11)C1—C2B—H2C107.6
C2B—C1—C2Bi102.4 (2)S1B—C2B—H2C107.6
C1—C2A—S1A117.38 (12)C1—C2B—H2D107.6
C1—C2A—H2A108.0S1B—C2B—H2D107.6
S1A—C2A—H2A108.0H2C—C2B—H2D107.0
C1—C2A—H2B108.0C5B—S1B—C2B103.38 (10)
S1A—C2A—H2B108.0C5B—N1B—N2B107.95 (16)
H2A—C2A—H2B107.2C5B—N1B—C6B129.62 (17)
C5A—S1A—C2A99.51 (10)N2B—N1B—C6B122.38 (16)
C5A—N1A—N2A107.25 (18)N3B—N2B—N1B106.18 (16)
C5A—N1A—C6A132.18 (18)N2B—N3B—N4B111.69 (16)
N2A—N1A—C6A120.57 (17)C5B—N4B—N3B105.38 (16)
N3A—N2A—N1A106.87 (18)N4B—C5B—N1B108.81 (17)
N2A—N3A—N4A111.1 (2)N4B—C5B—S1B130.22 (15)
C5A—N4A—N3A105.96 (18)N1B—C5B—S1B120.97 (15)
N4A—C5A—N1A108.80 (18)C7B—C6B—C11B122.0 (2)
N4A—C5A—S1A127.10 (16)C7B—C6B—N1B119.04 (18)
N1A—C5A—S1A124.04 (17)C11B—C6B—N1B118.92 (19)
C11A—C6A—C7A121.2 (2)C6B—C7B—C8B118.5 (2)
C11A—C6A—N1A119.93 (19)C6B—C7B—H7B120.8
C7A—C6A—N1A118.9 (2)C8B—C7B—H7B120.8
C6A—C7A—C8A118.4 (3)C9B—C8B—C7B120.1 (3)
C6A—C7A—H7A120.8C9B—C8B—H8B119.9
C8A—C7A—H7A120.8C7B—C8B—H8B119.9
C7A—C8A—C9A120.6 (3)C8B—C9B—C10B120.7 (2)
C7A—C8A—H8A119.7C8B—C9B—H9B119.6
C9A—C8A—H8A119.7C10B—C9B—H9B119.6
C10A—C9A—C8A120.0 (3)C9B—C10B—C11B120.2 (2)
C10A—C9A—H9A120.0C9B—C10B—H10B119.9
C8A—C9A—H9A120.0C11B—C10B—H10B119.9
C9A—C10A—C11A120.5 (3)C6B—C11B—C10B118.4 (2)
C9A—C10A—H10A119.8C6B—C11B—H11B120.8
C11A—C10A—H10A119.8C10B—C11B—H11B120.8
C2Ai—C1—C2A—S1A56.77 (11)C2A—C1—C2B—S1B68.41 (19)
C2B—C1—C2A—S1A65.0 (2)C2Ai—C1—C2B—S1B55.80 (18)
C2Bi—C1—C2A—S1A177.66 (14)C2Bi—C1—C2B—S1B176.06 (18)
C1—C2A—S1A—C5A96.39 (16)C1—C2B—S1B—C5B95.74 (14)
C5A—N1A—N2A—N3A0.9 (3)C5B—N1B—N2B—N3B0.2 (2)
C6A—N1A—N2A—N3A178.6 (2)C6B—N1B—N2B—N3B177.42 (19)
N1A—N2A—N3A—N4A0.2 (3)N1B—N2B—N3B—N4B0.0 (2)
N2A—N3A—N4A—C5A0.7 (3)N2B—N3B—N4B—C5B0.2 (2)
N3A—N4A—C5A—N1A1.3 (3)N3B—N4B—C5B—N1B0.3 (2)
N3A—N4A—C5A—S1A176.21 (18)N3B—N4B—C5B—S1B179.69 (17)
N2A—N1A—C5A—N4A1.4 (2)N2B—N1B—C5B—N4B0.3 (2)
C6A—N1A—C5A—N4A178.1 (2)C6B—N1B—C5B—N4B177.1 (2)
N2A—N1A—C5A—S1A176.18 (16)N2B—N1B—C5B—S1B179.68 (14)
C6A—N1A—C5A—S1A4.4 (3)C6B—N1B—C5B—S1B2.9 (3)
C2A—S1A—C5A—N4A6.2 (2)C2B—S1B—C5B—N4B16.1 (2)
C2A—S1A—C5A—N1A176.63 (17)C2B—S1B—C5B—N1B163.90 (17)
C5A—N1A—C6A—C11A39.0 (3)C5B—N1B—C6B—C7B65.8 (3)
N2A—N1A—C6A—C11A140.4 (2)N2B—N1B—C6B—C7B117.1 (2)
C5A—N1A—C6A—C7A142.7 (3)C5B—N1B—C6B—C11B115.4 (2)
N2A—N1A—C6A—C7A37.9 (3)N2B—N1B—C6B—C11B61.7 (3)
C11A—C6A—C7A—C8A0.8 (4)C11B—C6B—C7B—C8B1.8 (3)
N1A—C6A—C7A—C8A177.5 (3)N1B—C6B—C7B—C8B179.5 (2)
C6A—C7A—C8A—C9A0.6 (5)C6B—C7B—C8B—C9B1.6 (4)
C7A—C8A—C9A—C10A0.0 (6)C7B—C8B—C9B—C10B0.1 (4)
C8A—C9A—C10A—C11A0.3 (5)C8B—C9B—C10B—C11B1.3 (4)
C9A—C10A—C11A—C6A0.1 (4)C7B—C6B—C11B—C10B0.4 (3)
C7A—C6A—C11A—C10A0.5 (4)N1B—C6B—C11B—C10B179.18 (19)
N1A—C6A—C11A—C10A177.8 (2)C9B—C10B—C11B—C6B1.1 (4)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2A—H2A···N2Bii0.972.573.409 (3)145
C10B—H10B···N3Aiii0.932.603.478 (4)157
Symmetry codes: (ii) x, y, z+1/2; (iii) x, y+1, z1/2.
 

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