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The crystal packing of the title compound, C21H16N2S9, involves weak inter­molecular C—H...S inter­actions and inter­planar π–π stacking, generating a three-dimensional supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045545/hb2176sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045545/hb2176Isup2.hkl
Contains datablock I

CCDC reference: 629830

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.092
  • Data-to-parameter ratio = 19.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT322_ALERT_2_C Check Hybridisation of S8 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S9 in Main Residue . ?
0 ALERT level A = In general: serious problem 1 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 1 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: APEX2 (Bruker 2004); cell refinement: APEX2; data reduction: SAINT (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL.

4,5-Bis{2-[(benzothiazol-2-yl)sulfanyl]ethylsulfanyl}-1,3-dithiole-2-thione top
Crystal data top
C21H16N2S9Z = 2
Mr = 584.90F(000) = 600
Triclinic, P1Dx = 1.544 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4940 (11) ÅCell parameters from 3068 reflections
b = 10.7870 (13) Åθ = 2.8–27.2°
c = 13.8470 (17) ŵ = 0.81 mm1
α = 110.536 (1)°T = 291 K
β = 105.588 (1)°Plate, yellow
γ = 93.947 (1)°0.34 × 0.23 × 0.11 mm
V = 1258.0 (3) Å3
Data collection top
Bruker APEX2 CCD
diffractometer
5510 independent reflections
Radiation source: fine-focus sealed tube3908 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1212
Tmin = 0.769, Tmax = 0.915k = 1413
10333 measured reflectionsl = 1717
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0354P)2 + 0.384P]
where P = (Fo2 + 2Fc2)/3
5510 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

Experimental. 1H NMR (400 MHz): δ 7.90 (d, J = 7.96 Hz, ArH), 7.74 (d, J = 7.88 Hz, ArH), 7.41 (t, J = 7.64 Hz, ArH), 7.30 (t, J = 7.58 Hz, ArH), 3.62 (t, J = 7.62 Hz, SCH2), 3.37 (t, J = 7.60 Hz, SCH2).

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
S10.26218 (7)0.06348 (8)0.17740 (7)0.0786 (2)
S20.49215 (7)0.00225 (7)0.34002 (6)0.06511 (19)
S30.56999 (6)0.05729 (6)0.17059 (5)0.05627 (17)
S40.79998 (8)0.03401 (7)0.44502 (6)0.06498 (19)
S50.89472 (7)0.03103 (8)0.25537 (6)0.0663 (2)
S60.90095 (7)0.39183 (7)0.67577 (6)0.0678 (2)
S70.95825 (7)0.27641 (8)0.06907 (6)0.0708 (2)
S80.67306 (7)0.55168 (7)0.73887 (5)0.05922 (17)
S90.73054 (8)0.33234 (8)0.09981 (6)0.0686 (2)
N10.6078 (2)0.33832 (19)0.56054 (15)0.0517 (5)
N20.6664 (2)0.2722 (2)0.05112 (16)0.0565 (5)
C10.4318 (2)0.0419 (2)0.2281 (2)0.0557 (6)
C20.6777 (2)0.0045 (2)0.3442 (2)0.0525 (6)
C30.7145 (2)0.0300 (2)0.26513 (19)0.0485 (5)
C40.8194 (3)0.1156 (3)0.5649 (2)0.0588 (6)
H4A0.72230.12530.57370.071*
H4B0.88140.10440.62850.071*
C50.8869 (3)0.2416 (2)0.5584 (2)0.0568 (6)
H5A0.82680.25110.49350.068*
H5B0.98540.23310.55200.068*
C60.8873 (3)0.0790 (2)0.14104 (19)0.0578 (6)
H6A0.94800.02920.10050.069*
H6B0.78570.05580.09300.069*
C70.9420 (3)0.2273 (2)0.1783 (2)0.0595 (6)
H7A1.03830.25210.23360.071*
H7B0.87390.27650.21110.071*
C80.7160 (3)0.4138 (2)0.64626 (19)0.0512 (6)
C90.7739 (3)0.2899 (2)0.01356 (19)0.0542 (6)
C100.4768 (2)0.3882 (2)0.56374 (17)0.0451 (5)
C110.3379 (3)0.3301 (2)0.48500 (19)0.0546 (6)
H110.32730.25310.42390.066*
C120.2173 (3)0.3889 (3)0.4996 (2)0.0592 (6)
H120.12440.35120.44770.071*
C130.2316 (3)0.5038 (3)0.5906 (2)0.0624 (7)
H130.14810.54130.59880.075*
C140.3671 (3)0.5629 (3)0.6687 (2)0.0591 (6)
H140.37650.63960.72970.071*
C150.4898 (2)0.5045 (2)0.65400 (18)0.0480 (5)
C160.5353 (3)0.2926 (2)0.01174 (19)0.0524 (6)
C170.3976 (3)0.2808 (3)0.0053 (2)0.0656 (7)
H170.38740.25680.06170.079*
C180.2783 (3)0.3049 (3)0.0617 (3)0.0743 (8)
H180.18650.29850.05020.089*
C190.2920 (3)0.3386 (3)0.1464 (3)0.0787 (8)
H190.20900.35500.19080.094*
C200.4252 (3)0.3487 (3)0.1668 (2)0.0757 (8)
H200.43310.37000.22490.091*
C210.5480 (3)0.3259 (2)0.0979 (2)0.0570 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0384 (3)0.0904 (5)0.0896 (5)0.0244 (3)0.0107 (3)0.0190 (4)
S20.0424 (3)0.0751 (4)0.0839 (5)0.0160 (3)0.0255 (3)0.0323 (4)
S30.0367 (3)0.0615 (4)0.0650 (4)0.0127 (3)0.0094 (3)0.0219 (3)
S40.0598 (4)0.0630 (4)0.0839 (5)0.0274 (3)0.0217 (3)0.0395 (4)
S50.0338 (3)0.0901 (5)0.0862 (5)0.0171 (3)0.0165 (3)0.0476 (4)
S60.0449 (4)0.0786 (5)0.0701 (4)0.0163 (3)0.0155 (3)0.0180 (4)
S70.0468 (4)0.0953 (5)0.0787 (5)0.0081 (4)0.0229 (3)0.0416 (4)
S80.0529 (4)0.0618 (4)0.0550 (4)0.0117 (3)0.0178 (3)0.0122 (3)
S90.0624 (4)0.0812 (5)0.0801 (5)0.0105 (4)0.0294 (4)0.0470 (4)
N10.0465 (11)0.0566 (12)0.0528 (11)0.0157 (9)0.0199 (9)0.0174 (9)
N20.0510 (12)0.0653 (13)0.0553 (12)0.0123 (10)0.0211 (10)0.0222 (10)
C10.0368 (12)0.0482 (13)0.0679 (16)0.0098 (10)0.0115 (11)0.0090 (11)
C20.0383 (12)0.0491 (13)0.0707 (16)0.0142 (10)0.0167 (11)0.0230 (12)
C30.0327 (11)0.0435 (12)0.0649 (15)0.0090 (9)0.0105 (10)0.0189 (11)
C40.0515 (14)0.0762 (17)0.0680 (16)0.0256 (13)0.0260 (12)0.0422 (14)
C50.0433 (13)0.0704 (16)0.0688 (16)0.0204 (12)0.0272 (12)0.0318 (13)
C60.0368 (12)0.0670 (16)0.0607 (15)0.0107 (11)0.0140 (11)0.0149 (12)
C70.0444 (13)0.0686 (16)0.0568 (15)0.0089 (12)0.0119 (11)0.0170 (13)
C80.0490 (13)0.0577 (14)0.0536 (14)0.0154 (11)0.0223 (11)0.0236 (12)
C90.0506 (14)0.0539 (14)0.0588 (14)0.0075 (11)0.0187 (11)0.0216 (12)
C100.0472 (13)0.0498 (12)0.0481 (12)0.0146 (10)0.0205 (10)0.0252 (10)
C110.0535 (14)0.0577 (14)0.0521 (14)0.0117 (12)0.0170 (11)0.0199 (12)
C120.0488 (14)0.0719 (17)0.0627 (16)0.0141 (12)0.0171 (12)0.0321 (14)
C130.0560 (16)0.0747 (17)0.0724 (17)0.0288 (13)0.0299 (13)0.0363 (15)
C140.0630 (16)0.0582 (15)0.0615 (15)0.0225 (13)0.0280 (13)0.0209 (12)
C150.0499 (13)0.0508 (13)0.0514 (13)0.0134 (11)0.0224 (11)0.0234 (11)
C160.0549 (14)0.0441 (12)0.0562 (14)0.0114 (11)0.0220 (11)0.0129 (11)
C170.0601 (17)0.0692 (17)0.0688 (17)0.0177 (14)0.0306 (14)0.0194 (14)
C180.0566 (17)0.0741 (19)0.090 (2)0.0194 (14)0.0286 (16)0.0235 (16)
C190.0585 (18)0.0708 (19)0.101 (2)0.0163 (14)0.0098 (16)0.0372 (17)
C200.073 (2)0.0763 (19)0.088 (2)0.0130 (15)0.0185 (16)0.0485 (17)
C210.0568 (15)0.0478 (13)0.0686 (16)0.0091 (11)0.0204 (13)0.0245 (12)
Geometric parameters (Å, º) top
S1—C11.642 (2)C5—H5B0.9700
S2—C11.713 (3)C6—C71.503 (3)
S2—C21.745 (2)C6—H6A0.9700
S3—C11.734 (3)C6—H6B0.9700
S3—C31.744 (2)C7—H7A0.9700
S4—C21.752 (2)C7—H7B0.9700
S4—C41.819 (3)C10—C151.395 (3)
S5—C31.752 (2)C10—C111.398 (3)
S5—C61.816 (3)C11—C121.375 (3)
S6—C81.745 (2)C11—H110.9300
S6—C51.815 (2)C12—C131.390 (3)
S7—C91.751 (2)C12—H120.9300
S7—C71.808 (3)C13—C141.374 (3)
S8—C151.740 (2)C13—H130.9300
S8—C81.747 (2)C14—C151.390 (3)
S9—C211.737 (3)C14—H140.9300
S9—C91.740 (2)C16—C211.393 (3)
N1—C81.296 (3)C16—C171.395 (3)
N1—C101.394 (3)C17—C181.363 (4)
N2—C91.295 (3)C17—H170.9300
N2—C161.394 (3)C18—C191.378 (4)
C2—C31.342 (3)C18—H180.9300
C4—C51.505 (3)C19—C201.373 (4)
C4—H4A0.9700C19—H190.9300
C4—H4B0.9700C20—C211.391 (4)
C5—H5A0.9700C20—H200.9300
C1—S2—C297.57 (12)N1—C8—S6125.85 (18)
C1—S3—C397.47 (12)N1—C8—S8116.84 (18)
C2—S4—C4100.88 (11)S6—C8—S8117.30 (14)
C3—S5—C6104.46 (11)N2—C9—S9116.86 (19)
C8—S6—C5100.15 (11)N2—C9—S7125.07 (19)
C9—S7—C7100.40 (11)S9—C9—S7118.06 (14)
C15—S8—C888.55 (11)N1—C10—C15115.6 (2)
C21—S9—C988.54 (12)N1—C10—C11124.9 (2)
C8—N1—C10109.67 (19)C15—C10—C11119.5 (2)
C9—N2—C16109.8 (2)C12—C11—C10118.7 (2)
S1—C1—S2125.16 (16)C12—C11—H11120.7
S1—C1—S3121.99 (16)C10—C11—H11120.7
S2—C1—S3112.85 (13)C11—C12—C13121.2 (2)
C3—C2—S2116.39 (18)C11—C12—H12119.4
C3—C2—S4124.52 (18)C13—C12—H12119.4
S2—C2—S4119.01 (15)C14—C13—C12121.0 (2)
C2—C3—S3115.65 (17)C14—C13—H13119.5
C2—C3—S5122.11 (18)C12—C13—H13119.5
S3—C3—S5122.22 (15)C13—C14—C15118.1 (2)
C5—C4—S4112.56 (17)C13—C14—H14121.0
C5—C4—H4A109.1C15—C14—H14121.0
S4—C4—H4A109.1C14—C15—C10121.5 (2)
C5—C4—H4B109.1C14—C15—S8129.09 (19)
S4—C4—H4B109.1C10—C15—S8109.34 (17)
H4A—C4—H4B107.8C21—C16—N2115.2 (2)
C4—C5—S6112.74 (17)C21—C16—C17119.7 (2)
C4—C5—H5A109.0N2—C16—C17125.1 (2)
S6—C5—H5A109.0C18—C17—C16119.1 (3)
C4—C5—H5B109.0C18—C17—H17120.5
S6—C5—H5B109.0C16—C17—H17120.5
H5A—C5—H5B107.8C17—C18—C19120.9 (3)
C7—C6—S5111.25 (17)C17—C18—H18119.6
C7—C6—H6A109.4C19—C18—H18119.6
S5—C6—H6A109.4C20—C19—C18121.6 (3)
C7—C6—H6B109.4C20—C19—H19119.2
S5—C6—H6B109.4C18—C19—H19119.2
H6A—C6—H6B108.0C19—C20—C21117.9 (3)
C6—C7—S7112.82 (17)C19—C20—H20121.0
C6—C7—H7A109.0C21—C20—H20121.0
S7—C7—H7A109.0C20—C21—C16120.8 (2)
C6—C7—H7B109.0C20—C21—S9129.6 (2)
S7—C7—H7B109.0C16—C21—S9109.56 (18)
H7A—C7—H7B107.8
C2—S2—C1—S1177.60 (16)C7—S7—C9—N22.5 (2)
C2—S2—C1—S32.66 (15)C7—S7—C9—S9178.45 (14)
C3—S3—C1—S1177.64 (15)C8—N1—C10—C150.7 (3)
C3—S3—C1—S22.61 (15)C8—N1—C10—C11178.9 (2)
C1—S2—C2—C31.7 (2)N1—C10—C11—C12178.8 (2)
C1—S2—C2—S4178.64 (14)C15—C10—C11—C120.7 (3)
C4—S4—C2—C3111.8 (2)C10—C11—C12—C130.1 (4)
C4—S4—C2—S271.58 (16)C11—C12—C13—C140.4 (4)
S2—C2—C3—S30.1 (2)C12—C13—C14—C150.1 (4)
S4—C2—C3—S3176.86 (13)C13—C14—C15—C101.0 (4)
S2—C2—C3—S5178.11 (12)C13—C14—C15—S8177.93 (19)
S4—C2—C3—S51.4 (3)N1—C10—C15—C14178.3 (2)
C1—S3—C3—C21.5 (2)C11—C10—C15—C141.3 (3)
C1—S3—C3—S5179.75 (14)N1—C10—C15—S80.8 (2)
C6—S5—C3—C2177.03 (19)C11—C10—C15—S8178.76 (17)
C6—S5—C3—S34.84 (17)C8—S8—C15—C14177.8 (2)
C2—S4—C4—C562.09 (19)C8—S8—C15—C100.54 (17)
S4—C4—C5—S6178.10 (12)C9—N2—C16—C210.1 (3)
C8—S6—C5—C476.37 (19)C9—N2—C16—C17179.5 (2)
C3—S5—C6—C796.39 (18)C21—C16—C17—C181.3 (4)
S5—C6—C7—S7172.86 (12)N2—C16—C17—C18179.3 (2)
C9—S7—C7—C682.42 (19)C16—C17—C18—C190.9 (4)
C10—N1—C8—S6178.76 (17)C17—C18—C19—C200.3 (5)
C10—N1—C8—S80.2 (3)C18—C19—C20—C211.1 (4)
C5—S6—C8—N10.9 (2)C19—C20—C21—C160.7 (4)
C5—S6—C8—S8179.48 (14)C19—C20—C21—S9179.2 (2)
C15—S8—C8—N10.21 (19)N2—C16—C21—C20179.9 (2)
C15—S8—C8—S6178.48 (15)C17—C16—C21—C200.5 (4)
C16—N2—C9—S90.0 (3)N2—C16—C21—S90.1 (3)
C16—N2—C9—S7179.13 (17)C17—C16—C21—S9179.60 (19)
C21—S9—C9—N20.1 (2)C9—S9—C21—C20180.0 (3)
C21—S9—C9—S7179.26 (15)C9—S9—C21—C160.12 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···S1i0.972.833.482 (3)125
Symmetry code: (i) x+1, y, z.
 

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