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In the mol­ecule of the title compound, C14H10ClN3S2, the dithio­lane ring adopts an envelope conformation. The intra­molecular C—H...Cl hydrogen bond may be effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040736/hk2138sup1.cif
Contains datablocks I, x, x1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040736/hk2138Isup2.hkl
Contains datablock I

CCDC reference: 627796

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.059
  • wR factor = 0.160
  • Data-to-parameter ratio = 8.1

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.07 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.43 Ang. PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.20
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.97 From the CIF: _reflns_number_total 1469 Count of symmetry unique reflns 1472 Completeness (_total/calc) 99.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

(E)-[4-(2-Chlorophenyl)-1,3-dithiolan-2-ylidene]-1-imidazolyl-acetonitrile top
Crystal data top
C14H10ClN3S2F(000) = 328
Mr = 319.82Dx = 1.505 Mg m3
Monoclinic, P21Melting point: 141.5 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 5.5690 (11) ÅCell parameters from 25 reflections
b = 9.5120 (19) Åθ = 9–13°
c = 13.372 (3) ŵ = 0.56 mm1
β = 95.05 (3)°T = 294 K
V = 705.6 (3) Å3Block, yellow
Z = 20.40 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1306 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.102
Graphite monochromatorθmax = 26.0°, θmin = 1.5°
ω/2θ scansh = 06
Absorption correction: ψ scan
(North et al., 1968)
k = 011
Tmin = 0.808, Tmax = 0.897l = 1616
1620 measured reflections3 standard reflections every 120 min
1469 independent reflections intensity decay: none
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059 w = 1/[σ2(Fo2) + (0.1P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.160(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.99 e Å3
1469 reflectionsΔρmin = 0.48 e Å3
181 parametersExtinction correction: SHELXL97
1 restraintExtinction coefficient: 0.094 (12)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with no Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.0 (2)
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
xyzUiso*/Ueq
Cl1.0713 (4)0.6876 (3)0.54197 (17)0.0667 (6)
S10.6821 (3)0.86502 (18)0.87800 (11)0.0431 (4)
S20.9283 (3)1.01255 (19)0.72387 (11)0.0451 (5)
N11.3816 (11)1.2196 (8)0.8766 (5)0.0603 (18)
N20.9976 (9)1.0482 (6)1.0250 (3)0.0386 (12)
N30.8268 (12)1.0893 (9)1.1646 (5)0.0597 (18)
C10.5819 (15)0.8890 (9)0.3648 (5)0.058 (2)
H1A0.54180.89640.29600.070*
C20.4508 (14)0.9610 (9)0.4320 (6)0.0568 (19)
H2A0.32221.01750.40790.068*
C30.5077 (13)0.9501 (9)0.5318 (5)0.0501 (18)
H3B0.41881.00070.57520.060*
C40.6978 (11)0.8643 (8)0.5719 (4)0.0413 (14)
C50.8255 (12)0.7961 (8)0.5037 (5)0.0450 (15)
C60.7702 (13)0.8073 (9)0.4014 (5)0.0522 (17)
H6A0.86150.75920.35750.063*
C70.7686 (11)0.8515 (8)0.6834 (5)0.0445 (15)
H7A0.87970.77200.69450.053*
C80.5675 (12)0.8331 (9)0.7489 (5)0.0492 (18)
H8A0.50360.73840.74200.059*
H8B0.43860.89870.72920.059*
C90.8994 (10)0.9877 (7)0.8510 (4)0.0344 (13)
C101.0378 (11)1.0579 (7)0.9224 (4)0.0390 (14)
C111.2279 (12)1.1483 (9)0.8958 (5)0.0460 (16)
C121.1362 (12)0.9815 (8)1.1002 (5)0.0459 (16)
H12A1.27720.93081.09440.055*
C131.0247 (14)1.0048 (10)1.1856 (5)0.0573 (19)
H13A1.07520.96871.24860.069*
C140.8159 (13)1.1098 (9)1.0706 (5)0.0499 (17)
H14A0.69461.16231.03610.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0527 (10)0.0630 (12)0.0844 (14)0.0137 (10)0.0061 (9)0.0074 (11)
S10.0442 (8)0.0492 (9)0.0363 (7)0.0095 (8)0.0052 (6)0.0034 (7)
S20.0484 (9)0.0544 (10)0.0326 (7)0.0183 (8)0.0040 (6)0.0004 (7)
N10.047 (3)0.072 (5)0.061 (4)0.020 (3)0.001 (3)0.009 (3)
N20.034 (2)0.048 (3)0.034 (3)0.004 (2)0.002 (2)0.001 (2)
N30.052 (3)0.083 (5)0.046 (3)0.001 (4)0.012 (3)0.011 (4)
C10.077 (5)0.058 (5)0.038 (3)0.001 (4)0.003 (3)0.001 (3)
C20.057 (4)0.056 (5)0.055 (4)0.008 (4)0.006 (3)0.003 (4)
C30.047 (4)0.053 (5)0.050 (4)0.005 (3)0.005 (3)0.006 (3)
C40.039 (3)0.041 (3)0.044 (3)0.013 (3)0.000 (2)0.002 (3)
C50.042 (3)0.033 (3)0.060 (4)0.003 (3)0.005 (3)0.001 (3)
C60.063 (4)0.043 (4)0.052 (4)0.002 (4)0.014 (3)0.009 (3)
C70.043 (3)0.047 (4)0.044 (3)0.000 (3)0.004 (3)0.002 (3)
C80.052 (4)0.055 (5)0.040 (3)0.020 (3)0.002 (3)0.001 (3)
C90.031 (3)0.037 (3)0.035 (3)0.006 (3)0.000 (2)0.001 (3)
C100.037 (3)0.042 (3)0.037 (3)0.001 (3)0.001 (2)0.002 (3)
C110.041 (3)0.055 (4)0.039 (3)0.000 (3)0.008 (3)0.002 (3)
C120.039 (3)0.051 (4)0.046 (3)0.005 (3)0.008 (3)0.001 (3)
C130.066 (4)0.067 (5)0.037 (3)0.009 (5)0.006 (3)0.005 (4)
C140.042 (3)0.064 (5)0.043 (4)0.009 (4)0.001 (3)0.005 (4)
Geometric parameters (Å, º) top
Cl—C51.754 (7)C3—C41.406 (10)
S1—C91.742 (7)C3—H3B0.9300
S1—C81.813 (6)C4—C51.368 (9)
S2—C91.738 (6)C4—C71.514 (8)
S2—C71.829 (7)C5—C61.380 (10)
N1—C111.139 (10)C6—H6A0.9300
N2—C141.360 (9)C7—C81.491 (9)
N2—C121.369 (8)C7—H7A0.9800
N2—C101.413 (8)C8—H8A0.9700
N3—C141.267 (9)C8—H8B0.9700
N3—C131.373 (11)C9—C101.350 (9)
C1—C61.361 (11)C10—C111.433 (10)
C1—C21.387 (11)C12—C131.364 (10)
C1—H1A0.9300C12—H12A0.9300
C2—C31.348 (10)C13—H13A0.9300
C2—H2A0.9300C14—H14A0.9300
C9—S1—C896.2 (3)C4—C7—S2107.6 (5)
C9—S2—C795.2 (3)C8—C7—H7A108.5
C14—N2—C12105.3 (5)C4—C7—H7A108.5
C14—N2—C10126.5 (5)S2—C7—H7A108.5
C12—N2—C10128.1 (5)C7—C8—S1108.7 (5)
C14—N3—C13105.1 (6)C7—C8—H8A110.0
C6—C1—C2118.8 (6)S1—C8—H8A110.0
C6—C1—H1A120.6C7—C8—H8B110.0
C2—C1—H1A120.6S1—C8—H8B110.0
C3—C2—C1120.8 (7)H8A—C8—H8B108.3
C3—C2—H2A119.6C10—C9—S2121.9 (5)
C1—C2—H2A119.6C10—C9—S1123.3 (5)
C2—C3—C4121.7 (7)S2—C9—S1114.8 (3)
C2—C3—H3B119.1C9—C10—N2121.7 (6)
C4—C3—H3B119.1C9—C10—C11120.7 (6)
C5—C4—C3116.1 (6)N2—C10—C11117.6 (6)
C5—C4—C7120.9 (6)N1—C11—C10178.6 (7)
C3—C4—C7123.0 (6)C13—C12—N2105.7 (6)
C4—C5—C6122.7 (7)C13—C12—H12A127.2
C4—C5—Cl121.5 (5)N2—C12—H12A127.2
C6—C5—Cl115.8 (6)C12—C13—N3109.9 (6)
C1—C6—C5119.9 (7)C12—C13—H13A125.0
C1—C6—H6A120.1N3—C13—H13A125.0
C5—C6—H6A120.1N3—C14—N2113.9 (7)
C8—C7—C4116.3 (5)N3—C14—H14A123.0
C8—C7—S2107.2 (5)N2—C14—H14A123.0
C6—C1—C2—C30.3 (13)C7—S2—C9—C10162.9 (5)
C1—C2—C3—C41.1 (13)C7—S2—C9—S116.5 (4)
C2—C3—C4—C51.8 (11)C8—S1—C9—C10175.6 (6)
C2—C3—C4—C7179.0 (7)C8—S1—C9—S25.0 (4)
C3—C4—C5—C61.3 (10)S2—C9—C10—N2173.5 (5)
C7—C4—C5—C6178.6 (7)S1—C9—C10—N27.1 (9)
C3—C4—C5—Cl178.9 (6)S2—C9—C10—C114.9 (9)
C7—C4—C5—Cl1.6 (9)S1—C9—C10—C11174.5 (5)
C2—C1—C6—C50.8 (12)C14—N2—C10—C974.5 (10)
C4—C5—C6—C10.0 (12)C12—N2—C10—C9108.8 (8)
Cl—C5—C6—C1179.9 (6)C14—N2—C10—C11104.0 (8)
C5—C4—C7—C8137.7 (7)C12—N2—C10—C1172.7 (9)
C3—C4—C7—C845.2 (10)C14—N2—C12—C131.5 (8)
C5—C4—C7—S2102.1 (7)C10—N2—C12—C13178.7 (7)
C3—C4—C7—S274.9 (7)N2—C12—C13—N32.6 (9)
C9—S2—C7—C837.4 (5)C14—N3—C13—C122.7 (10)
C9—S2—C7—C4163.2 (4)C13—N3—C14—N21.7 (10)
C4—C7—C8—S1165.6 (5)C12—N2—C14—N30.2 (9)
S2—C7—C8—S145.2 (6)C10—N2—C14—N3177.1 (7)
C9—S1—C8—C731.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···Cl0.982.523.068 (7)116
 

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