The title compound, C
18H
16N
8S
2, crystallizes in the monoclinic space group
P2
1/
c. The two 1-phenyl-1
H-tetrazole-5-thiol moieties are located on the same side of the butene-1,4-diyl plane but point in opposite directions. Intermolecular N
S interactions link the molecules to form one-dimensional polymeric chains along the
a axis.
Supporting information
CCDC reference: 242366
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.097
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.01 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 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
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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART or SAINT?; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
trans-5,5'-[(2-Butene-1,4-diyl)dithio]bis(1-phenyl-1,2,3,4-tetrazole)
top
Crystal data top
C18H16N8S2 | F(000) = 848 |
Mr = 408.51 | Dx = 1.392 Mg m−3 |
Monoclinic, P21/c | Melting point: 405 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.727 (3) Å | Cell parameters from 893 reflections |
b = 12.770 (4) Å | θ = 3.1–23.4° |
c = 15.947 (6) Å | µ = 0.30 mm−1 |
β = 100.332 (6)° | T = 293 K |
V = 1948.7 (11) Å3 | Prism, colourless |
Z = 4 | 0.24 × 0.20 × 0.16 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3987 independent reflections |
Radiation source: fine-focus sealed tube | 2561 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ψ and ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→9 |
Tmin = 0.928, Tmax = 0.954 | k = −12→15 |
11016 measured reflections | l = −17→19 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.1948P] where P = (Fo2 + 2Fc2)/3 |
3987 reflections | (Δ/σ)max = 0.002 |
253 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Special details top
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 | |
S1 | 0.94012 (5) | −0.01410 (4) | 0.16461 (4) | 0.05021 (17) | |
S2 | 0.56451 (5) | 0.10776 (4) | −0.14436 (4) | 0.05116 (17) | |
N1 | 0.84945 (17) | 0.18624 (14) | 0.17421 (11) | 0.0470 (4) | |
N2 | 0.68139 (18) | 0.07358 (16) | 0.16311 (14) | 0.0620 (6) | |
N3 | 0.6311 (2) | 0.17264 (18) | 0.16686 (16) | 0.0743 (6) | |
N4 | 0.7300 (2) | 0.24115 (16) | 0.17412 (14) | 0.0664 (6) | |
N5 | 0.67510 (18) | 0.29875 (14) | −0.10188 (11) | 0.0480 (4) | |
N6 | 0.83367 (18) | 0.18473 (15) | −0.11681 (13) | 0.0583 (5) | |
N7 | 0.8916 (2) | 0.28087 (18) | −0.09981 (15) | 0.0715 (6) | |
N8 | 0.8000 (2) | 0.35044 (16) | −0.09111 (14) | 0.0654 (6) | |
C1 | 0.9811 (2) | 0.23763 (17) | 0.17667 (13) | 0.0452 (5) | |
C2 | 1.0971 (2) | 0.20098 (18) | 0.23056 (14) | 0.0527 (6) | |
H2 | 1.0900 | 0.1451 | 0.2670 | 0.063* | |
C3 | 1.2241 (2) | 0.2480 (2) | 0.22998 (17) | 0.0644 (7) | |
H3 | 1.3039 | 0.2228 | 0.2652 | 0.077* | |
C4 | 1.2334 (3) | 0.3308 (2) | 0.1784 (2) | 0.0750 (8) | |
H4 | 1.3199 | 0.3618 | 0.1781 | 0.090* | |
C5 | 1.1175 (3) | 0.3695 (2) | 0.12670 (19) | 0.0768 (8) | |
H5 | 1.1249 | 0.4281 | 0.0931 | 0.092* | |
C6 | 0.9883 (3) | 0.32171 (19) | 0.12401 (16) | 0.0607 (6) | |
H6 | 0.9092 | 0.3460 | 0.0876 | 0.073* | |
C7 | 0.8179 (2) | 0.08359 (17) | 0.16754 (13) | 0.0447 (5) | |
C8 | 0.8330 (2) | −0.10676 (16) | 0.09474 (14) | 0.0476 (5) | |
H8A | 0.8787 | −0.1746 | 0.0992 | 0.057* | |
H8B | 0.7436 | −0.1147 | 0.1129 | 0.057* | |
C9 | 0.8094 (2) | −0.07177 (16) | 0.00485 (14) | 0.0482 (5) | |
H9 | 0.8870 | −0.0656 | −0.0215 | 0.058* | |
C10 | 0.6880 (2) | −0.04913 (16) | −0.03975 (14) | 0.0476 (5) | |
H10 | 0.6110 | −0.0551 | −0.0129 | 0.057* | |
C11 | 0.6618 (2) | −0.01445 (16) | −0.13034 (14) | 0.0475 (5) | |
H11A | 0.6096 | −0.0683 | −0.1654 | 0.057* | |
H11B | 0.7504 | −0.0053 | −0.1492 | 0.057* | |
C12 | 0.6987 (2) | 0.19758 (16) | −0.11852 (13) | 0.0448 (5) | |
C13 | 0.5475 (2) | 0.35120 (17) | −0.09497 (14) | 0.0468 (5) | |
C14 | 0.5113 (3) | 0.44014 (18) | −0.14219 (16) | 0.0591 (6) | |
H14 | 0.5683 | 0.4659 | −0.1784 | 0.071* | |
C15 | 0.3883 (3) | 0.4906 (2) | −0.13476 (19) | 0.0780 (8) | |
H15 | 0.3633 | 0.5522 | −0.1648 | 0.094* | |
C16 | 0.3033 (3) | 0.4499 (2) | −0.0830 (2) | 0.0855 (9) | |
H16 | 0.2199 | 0.4835 | −0.0790 | 0.103* | |
C17 | 0.3395 (3) | 0.3608 (2) | −0.03732 (19) | 0.0778 (8) | |
H17 | 0.2801 | 0.3332 | −0.0033 | 0.093* | |
C18 | 0.4644 (3) | 0.31147 (19) | −0.04161 (15) | 0.0613 (7) | |
H18 | 0.4917 | 0.2523 | −0.0089 | 0.074* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0376 (3) | 0.0485 (3) | 0.0633 (4) | 0.0016 (3) | 0.0056 (2) | 0.0030 (3) |
S2 | 0.0382 (3) | 0.0442 (3) | 0.0687 (4) | 0.0038 (2) | 0.0029 (3) | −0.0005 (3) |
N1 | 0.0386 (10) | 0.0474 (11) | 0.0539 (11) | 0.0028 (9) | 0.0051 (8) | −0.0026 (9) |
N2 | 0.0388 (11) | 0.0603 (13) | 0.0882 (16) | 0.0005 (10) | 0.0147 (10) | −0.0056 (11) |
N3 | 0.0448 (12) | 0.0714 (16) | 0.1064 (19) | 0.0072 (12) | 0.0128 (11) | −0.0133 (13) |
N4 | 0.0475 (12) | 0.0596 (14) | 0.0906 (16) | 0.0107 (11) | 0.0081 (10) | −0.0090 (11) |
N5 | 0.0461 (11) | 0.0429 (11) | 0.0538 (11) | −0.0036 (9) | 0.0060 (8) | 0.0003 (9) |
N6 | 0.0421 (11) | 0.0553 (13) | 0.0765 (14) | −0.0008 (10) | 0.0077 (9) | −0.0031 (10) |
N7 | 0.0498 (12) | 0.0671 (15) | 0.0969 (18) | −0.0067 (12) | 0.0114 (11) | −0.0059 (12) |
N8 | 0.0549 (13) | 0.0561 (13) | 0.0831 (16) | −0.0135 (11) | 0.0073 (10) | −0.0044 (11) |
C1 | 0.0454 (12) | 0.0449 (13) | 0.0464 (13) | −0.0025 (10) | 0.0112 (10) | −0.0076 (10) |
C2 | 0.0508 (13) | 0.0519 (14) | 0.0540 (14) | −0.0056 (11) | 0.0051 (11) | −0.0039 (11) |
C3 | 0.0517 (15) | 0.0672 (17) | 0.0722 (18) | −0.0091 (13) | 0.0049 (12) | −0.0192 (14) |
C4 | 0.0674 (18) | 0.074 (2) | 0.088 (2) | −0.0238 (16) | 0.0282 (16) | −0.0220 (16) |
C5 | 0.109 (2) | 0.0546 (17) | 0.077 (2) | −0.0138 (17) | 0.0423 (18) | 0.0017 (14) |
C6 | 0.0739 (17) | 0.0511 (15) | 0.0592 (16) | 0.0024 (13) | 0.0172 (13) | 0.0006 (12) |
C7 | 0.0399 (12) | 0.0473 (14) | 0.0469 (13) | 0.0005 (10) | 0.0075 (9) | 0.0014 (10) |
C8 | 0.0414 (12) | 0.0415 (12) | 0.0599 (15) | −0.0024 (10) | 0.0096 (10) | 0.0066 (10) |
C9 | 0.0418 (12) | 0.0446 (13) | 0.0607 (15) | −0.0018 (10) | 0.0161 (10) | −0.0013 (11) |
C10 | 0.0412 (12) | 0.0402 (12) | 0.0643 (15) | 0.0000 (10) | 0.0172 (11) | 0.0008 (10) |
C11 | 0.0416 (11) | 0.0442 (13) | 0.0563 (14) | 0.0038 (10) | 0.0081 (10) | −0.0053 (10) |
C12 | 0.0413 (12) | 0.0457 (13) | 0.0462 (13) | 0.0029 (10) | 0.0051 (9) | 0.0024 (10) |
C13 | 0.0544 (13) | 0.0406 (13) | 0.0441 (13) | 0.0020 (11) | 0.0050 (10) | −0.0069 (10) |
C14 | 0.0730 (16) | 0.0417 (13) | 0.0618 (16) | 0.0015 (13) | 0.0101 (12) | −0.0032 (12) |
C15 | 0.099 (2) | 0.0487 (16) | 0.082 (2) | 0.0227 (16) | 0.0049 (17) | −0.0058 (14) |
C16 | 0.086 (2) | 0.077 (2) | 0.096 (2) | 0.0288 (18) | 0.0223 (18) | −0.0252 (18) |
C17 | 0.0841 (19) | 0.076 (2) | 0.084 (2) | 0.0119 (17) | 0.0416 (16) | −0.0149 (16) |
C18 | 0.0755 (17) | 0.0552 (15) | 0.0569 (16) | 0.0093 (13) | 0.0222 (13) | −0.0006 (12) |
Geometric parameters (Å, º) top
S1—C7 | 1.730 (2) | C5—C6 | 1.391 (3) |
S1—C8 | 1.820 (2) | C5—H5 | 0.93 |
S2—C12 | 1.731 (2) | C6—H6 | 0.93 |
S2—C11 | 1.818 (2) | C8—C9 | 1.480 (3) |
N1—C7 | 1.346 (3) | C8—H8A | 0.97 |
N1—N4 | 1.357 (2) | C8—H8B | 0.97 |
N1—C1 | 1.433 (3) | C9—C10 | 1.297 (3) |
N2—C7 | 1.323 (3) | C9—H9 | 0.93 |
N2—N3 | 1.362 (3) | C10—C11 | 1.489 (3) |
N3—N4 | 1.291 (3) | C10—H10 | 0.93 |
N5—C12 | 1.347 (3) | C11—H11A | 0.97 |
N5—N8 | 1.366 (2) | C11—H11B | 0.97 |
N5—C13 | 1.432 (3) | C13—C18 | 1.372 (3) |
N6—C12 | 1.319 (3) | C13—C14 | 1.373 (3) |
N6—N7 | 1.358 (3) | C14—C15 | 1.382 (3) |
N7—N8 | 1.283 (3) | C14—H14 | 0.93 |
C1—C6 | 1.373 (3) | C15—C16 | 1.371 (4) |
C1—C2 | 1.373 (3) | C15—H15 | 0.93 |
C2—C3 | 1.375 (3) | C16—C17 | 1.363 (4) |
C2—H2 | 0.93 | C16—H16 | 0.93 |
C3—C4 | 1.353 (4) | C17—C18 | 1.380 (3) |
C3—H3 | 0.93 | C17—H17 | 0.93 |
C4—C5 | 1.364 (4) | C18—H18 | 0.93 |
C4—H4 | 0.93 | | |
| | | |
C7—S1—C8 | 99.46 (10) | S1—C8—H8A | 109.3 |
C12—S2—C11 | 100.73 (10) | C9—C8—H8B | 109.3 |
C7—N1—N4 | 108.66 (17) | S1—C8—H8B | 109.3 |
C7—N1—C1 | 129.66 (18) | H8A—C8—H8B | 108.0 |
N4—N1—C1 | 121.60 (18) | C10—C9—C8 | 124.5 (2) |
C7—N2—N3 | 105.86 (19) | C10—C9—H9 | 117.8 |
N4—N3—N2 | 111.42 (18) | C8—C9—H9 | 117.8 |
N3—N4—N1 | 105.94 (18) | C9—C10—C11 | 125.4 (2) |
C12—N5—N8 | 108.01 (18) | C9—C10—H10 | 117.3 |
C12—N5—C13 | 130.13 (18) | C11—C10—H10 | 117.3 |
N8—N5—C13 | 121.87 (18) | C10—C11—S2 | 111.70 (15) |
C12—N6—N7 | 105.54 (19) | C10—C11—H11A | 109.3 |
N8—N7—N6 | 112.08 (18) | S2—C11—H11A | 109.3 |
N7—N8—N5 | 105.73 (18) | C10—C11—H11B | 109.3 |
C6—C1—C2 | 121.5 (2) | S2—C11—H11B | 109.3 |
C6—C1—N1 | 119.0 (2) | H11A—C11—H11B | 107.9 |
C2—C1—N1 | 119.4 (2) | N6—C12—N5 | 108.62 (19) |
C1—C2—C3 | 119.1 (2) | N6—C12—S2 | 128.90 (17) |
C1—C2—H2 | 120.5 | N5—C12—S2 | 122.34 (16) |
C3—C2—H2 | 120.5 | C18—C13—C14 | 121.6 (2) |
C4—C3—C2 | 120.3 (2) | C18—C13—N5 | 119.4 (2) |
C4—C3—H3 | 119.9 | C14—C13—N5 | 119.1 (2) |
C2—C3—H3 | 119.9 | C13—C14—C15 | 118.7 (2) |
C3—C4—C5 | 120.8 (3) | C13—C14—H14 | 120.7 |
C3—C4—H4 | 119.6 | C15—C14—H14 | 120.7 |
C5—C4—H4 | 119.6 | C16—C15—C14 | 120.0 (3) |
C4—C5—C6 | 120.3 (3) | C16—C15—H15 | 120.0 |
C4—C5—H5 | 119.9 | C14—C15—H15 | 120.0 |
C6—C5—H5 | 119.9 | C17—C16—C15 | 120.8 (3) |
C1—C6—C5 | 118.0 (2) | C17—C16—H16 | 119.6 |
C1—C6—H6 | 121.0 | C15—C16—H16 | 119.6 |
C5—C6—H6 | 121.0 | C16—C17—C18 | 120.0 (3) |
N2—C7—N1 | 108.12 (19) | C16—C17—H17 | 120.0 |
N2—C7—S1 | 128.10 (18) | C18—C17—H17 | 120.0 |
N1—C7—S1 | 123.78 (16) | C13—C18—C17 | 118.9 (2) |
C9—C8—S1 | 111.65 (14) | C13—C18—H18 | 120.5 |
C9—C8—H8A | 109.3 | C17—C18—H18 | 120.5 |
| | | |
C7—N2—N3—N4 | −0.6 (3) | C8—S1—C7—N1 | −147.01 (18) |
N2—N3—N4—N1 | 0.7 (3) | C7—S1—C8—C9 | 74.83 (17) |
C7—N1—N4—N3 | −0.5 (3) | S1—C8—C9—C10 | −116.9 (2) |
C1—N1—N4—N3 | 176.53 (19) | C8—C9—C10—C11 | −179.59 (19) |
C12—N6—N7—N8 | 0.1 (3) | C9—C10—C11—S2 | −126.2 (2) |
N6—N7—N8—N5 | 0.6 (3) | C12—S2—C11—C10 | 84.12 (17) |
C12—N5—N8—N7 | −1.1 (2) | N7—N6—C12—N5 | −0.8 (2) |
C13—N5—N8—N7 | 178.79 (19) | N7—N6—C12—S2 | 174.91 (17) |
C7—N1—C1—C6 | 130.8 (2) | N8—N5—C12—N6 | 1.2 (2) |
N4—N1—C1—C6 | −45.6 (3) | C13—N5—C12—N6 | −178.7 (2) |
C7—N1—C1—C2 | −48.3 (3) | N8—N5—C12—S2 | −174.86 (15) |
N4—N1—C1—C2 | 135.3 (2) | C13—N5—C12—S2 | 5.3 (3) |
C6—C1—C2—C3 | −1.8 (3) | C11—S2—C12—N6 | 19.6 (2) |
N1—C1—C2—C3 | 177.33 (19) | C11—S2—C12—N5 | −165.29 (18) |
C1—C2—C3—C4 | 1.6 (3) | C12—N5—C13—C18 | 52.2 (3) |
C2—C3—C4—C5 | 0.5 (4) | N8—N5—C13—C18 | −127.6 (2) |
C3—C4—C5—C6 | −2.4 (4) | C12—N5—C13—C14 | −127.6 (2) |
C2—C1—C6—C5 | −0.1 (3) | N8—N5—C13—C14 | 52.5 (3) |
N1—C1—C6—C5 | −179.2 (2) | C18—C13—C14—C15 | 0.5 (3) |
C4—C5—C6—C1 | 2.2 (4) | N5—C13—C14—C15 | −179.6 (2) |
N3—N2—C7—N1 | 0.3 (3) | C13—C14—C15—C16 | −2.0 (4) |
N3—N2—C7—S1 | −179.13 (18) | C14—C15—C16—C17 | 1.1 (5) |
N4—N1—C7—N2 | 0.1 (2) | C15—C16—C17—C18 | 1.2 (5) |
C1—N1—C7—N2 | −176.6 (2) | C14—C13—C18—C17 | 1.8 (4) |
N4—N1—C7—S1 | 179.58 (16) | N5—C13—C18—C17 | −178.1 (2) |
C1—N1—C7—S1 | 2.8 (3) | C16—C17—C18—C13 | −2.7 (4) |
C8—S1—C7—N2 | 32.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···S1 | 0.93 | 2.84 | 3.226 (3) | 106 |
C8—H8A···N7i | 0.97 | 2.61 | 3.471 (3) | 148 |
C11—H11B···N6 | 0.97 | 2.58 | 3.030 (3) | 108 |
Symmetry code: (i) −x+2, −y, −z. |