Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structure of the title compound, C18H25NS6, at 180 K contains mol­ecules distorted significantly from planarity. The structure is non-centrosymmetric.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011482/bv2011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011482/bv2011Isup2.hkl
Contains datablock I

CCDC reference: 608382

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.084
  • Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.07
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.97 From the CIF: _reflns_number_total 4420 Count of symmetry unique reflns 2558 Completeness (_total/calc) 172.79% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1862 Fraction of Friedel pairs measured 0.728 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-[4,5-Bis(n-pentylsulfanyl)-1,3-dithiol-2-ylidene]-1,3-dithiolo[4,5-c]pyrrole top
Crystal data top
C18H25NS6F(000) = 944
Mr = 447.75Dx = 1.399 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 4175 reflections
a = 14.3456 (7) Åθ = 2.9–28.0°
b = 7.8603 (4) ŵ = 0.65 mm1
c = 18.9621 (9) ÅT = 180 K
β = 96.254 (1)°Needle, yellow
V = 2125.45 (18) Å30.35 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
4420 independent reflections
Radiation source: fine-focus sealed tube4209 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Thin–slice ω scansθmax = 28.0°, θmin = 3.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1814
Tmin = 0.756, Tmax = 0.938k = 910
7249 measured reflectionsl = 2325
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4420 reflectionsΔρmax = 0.45 e Å3
228 parametersΔρmin = 0.24 e Å3
2 restraintsAbsolute structure: Flack (1983), 1879 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (7)
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.7109 (0.0091) x - 6.9316 (0.0027) y - 2.0797 (0.0131) z = 5.3580 (0.0089)

* 0.0134 (0.0012) S1 * -0.0007 (0.0012) S2 * 0.0012 (0.0016) C1 * 0.0141 (0.0017) C2 * -0.0186 (0.0021) C3 * -0.0094 (0.0022) C4

Rms deviation of fitted atoms = 0.0116

5.0040 (0.0033) x - 7.3086 (0.0007) y + 1.4920 (0.0050) z = 4.1422 (0.0028)

Angle to previous plane (with approximate e.s.d.) = 12.52 (0.05)

* 0.0023 (0.0008) S1 * 0.0109 (0.0008) S2 * 0.0079 (0.0008) S3 * -0.0010 (0.0008) S4 * -0.0172 (0.0020) C5 * -0.0029 (0.0020) C6

Rms deviation of fitted atoms = 0.0091

0.7285 (0.0037) x - 7.0399 (0.0010) y + 8.2248 (0.0045) z = 2.3451 (0.0033)

Angle to previous plane (with approximate e.s.d.) = 25.53 (0.02)

* 0.0268 (0.0008) S3 * -0.0004 (0.0008) S4 * 0.0019 (0.0008) S5 * 0.0277 (0.0009) S6 * -0.0248 (0.0020) C7 * -0.0312 (0.0021) C8

Rms deviation of fitted atoms = 0.0226

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
S10.85735 (5)0.03419 (9)0.06984 (3)0.02576 (15)
S21.02041 (4)0.16466 (9)0.16788 (3)0.02466 (15)
S30.74054 (5)0.01857 (9)0.20689 (3)0.02409 (15)
S40.90056 (5)0.11133 (9)0.30062 (3)0.02568 (15)
S50.59715 (5)0.08246 (9)0.30305 (3)0.02566 (15)
S60.78444 (5)0.22771 (10)0.41392 (3)0.03009 (16)
N11.04999 (19)0.2520 (3)0.03287 (12)0.0341 (6)
H1B1.07700.28870.06950.041*
C10.9649 (2)0.1723 (4)0.03748 (14)0.0298 (6)
H1A0.92570.14610.07970.036*
C21.0877 (2)0.2672 (4)0.03629 (15)0.0317 (6)
H2A1.14640.31670.05290.038*
C30.9469 (2)0.1373 (3)0.03067 (14)0.0239 (5)
C41.0241 (2)0.1967 (3)0.07704 (13)0.0234 (5)
C50.90445 (19)0.0869 (3)0.15700 (13)0.0209 (5)
C60.85554 (19)0.0629 (3)0.21292 (13)0.0217 (5)
C70.71501 (19)0.0791 (3)0.28649 (13)0.0223 (5)
C80.7885 (2)0.1382 (3)0.32980 (13)0.0229 (5)
C90.5513 (2)0.2391 (4)0.23576 (16)0.0310 (6)
H9A0.50940.31870.25760.037*
H9B0.60450.30590.22120.037*
C100.4975 (2)0.1610 (4)0.16979 (15)0.0276 (6)
H10A0.48650.24980.13280.033*
H10B0.53630.07070.15120.033*
C110.4041 (2)0.0858 (4)0.18399 (15)0.0274 (6)
H11A0.37010.17060.21010.033*
H11B0.41600.01480.21510.033*
C120.3417 (2)0.0327 (4)0.11774 (16)0.0311 (6)
H12A0.33070.13230.08590.037*
H12B0.37440.05510.09220.037*
C130.2482 (2)0.0372 (4)0.13462 (19)0.0391 (7)
H13A0.21110.07240.09060.059*
H13B0.21420.05120.15790.059*
H13C0.25870.13540.16630.059*
C140.8325 (2)0.4391 (4)0.40025 (16)0.0360 (7)
H14A0.84300.49770.44670.043*
H14B0.89420.42600.38210.043*
C150.7707 (3)0.5507 (4)0.34915 (16)0.0386 (7)
H15A0.75740.48880.30370.046*
H15B0.80630.65450.33960.046*
C160.6775 (2)0.6044 (4)0.37429 (16)0.0359 (7)
H16A0.63920.66180.33470.043*
H16B0.64320.50120.38670.043*
C170.6879 (3)0.7220 (5)0.43755 (18)0.0422 (8)
H17A0.71710.82960.42390.051*
H17B0.73070.66900.47580.051*
C180.5950 (3)0.7628 (5)0.4662 (2)0.0543 (10)
H18A0.60590.84330.50560.081*
H18B0.56760.65790.48280.081*
H18C0.55170.81340.42830.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0260 (4)0.0338 (4)0.0182 (3)0.0021 (3)0.0055 (2)0.0004 (3)
S20.0203 (3)0.0348 (4)0.0196 (3)0.0017 (3)0.0053 (2)0.0023 (3)
S30.0232 (3)0.0284 (3)0.0222 (3)0.0005 (3)0.0090 (2)0.0043 (3)
S40.0196 (3)0.0401 (4)0.0179 (3)0.0062 (3)0.0046 (2)0.0008 (3)
S50.0202 (3)0.0336 (4)0.0250 (3)0.0015 (3)0.0106 (2)0.0004 (3)
S60.0306 (4)0.0440 (4)0.0166 (3)0.0057 (3)0.0073 (2)0.0028 (3)
N10.0413 (16)0.0397 (15)0.0245 (12)0.0008 (11)0.0180 (11)0.0060 (10)
C10.0369 (17)0.0327 (15)0.0215 (13)0.0060 (12)0.0106 (11)0.0007 (11)
C20.0322 (16)0.0344 (15)0.0314 (14)0.0008 (12)0.0155 (12)0.0029 (12)
C30.0285 (15)0.0210 (12)0.0234 (12)0.0063 (10)0.0080 (10)0.0000 (10)
C40.0267 (14)0.0241 (13)0.0208 (11)0.0064 (10)0.0092 (10)0.0044 (10)
C50.0207 (13)0.0246 (12)0.0179 (11)0.0048 (10)0.0046 (9)0.0002 (10)
C60.0216 (13)0.0256 (13)0.0185 (11)0.0053 (10)0.0049 (10)0.0029 (10)
C70.0233 (13)0.0250 (13)0.0203 (12)0.0054 (10)0.0106 (10)0.0036 (10)
C80.0249 (14)0.0293 (13)0.0158 (11)0.0064 (10)0.0076 (10)0.0029 (10)
C90.0264 (15)0.0253 (14)0.0419 (16)0.0073 (11)0.0059 (12)0.0046 (12)
C100.0234 (15)0.0294 (14)0.0304 (14)0.0082 (11)0.0054 (11)0.0061 (11)
C110.0223 (14)0.0304 (14)0.0303 (14)0.0071 (11)0.0068 (11)0.0024 (11)
C120.0287 (16)0.0313 (15)0.0332 (15)0.0068 (12)0.0028 (12)0.0016 (12)
C130.0300 (17)0.0369 (16)0.0497 (19)0.0034 (13)0.0007 (14)0.0025 (14)
C140.0281 (16)0.0480 (18)0.0325 (15)0.0032 (13)0.0061 (12)0.0126 (13)
C150.052 (2)0.0385 (17)0.0266 (14)0.0056 (15)0.0090 (14)0.0048 (12)
C160.0365 (18)0.0322 (15)0.0375 (16)0.0002 (13)0.0029 (13)0.0034 (13)
C170.042 (2)0.0465 (19)0.0390 (16)0.0019 (15)0.0072 (14)0.0031 (15)
C180.051 (2)0.045 (2)0.070 (3)0.0071 (17)0.0185 (19)0.0023 (18)
Geometric parameters (Å, º) top
S1—C31.751 (3)C10—H10A0.990
S1—C51.765 (3)C10—H10B0.990
S2—C41.747 (3)C11—C121.519 (4)
S2—C51.763 (3)C11—H11A0.990
S3—C61.762 (3)C11—H11B0.990
S3—C71.767 (3)C12—C131.517 (5)
S4—C61.759 (3)C12—H12A0.990
S4—C81.769 (3)C12—H12B0.990
S5—C71.753 (3)C13—H13A0.980
S5—C91.842 (3)C13—H13B0.980
S6—C81.750 (3)C13—H13C0.980
S6—C141.828 (3)C14—C151.519 (5)
N1—C11.367 (4)C14—H14A0.990
N1—C21.368 (4)C14—H14B0.990
N1—H1B0.880C15—C161.527 (5)
C1—C31.373 (4)C15—H15A0.990
C1—H1A0.950C15—H15B0.990
C2—C41.375 (4)C16—C171.509 (4)
C2—H2A0.950C16—H16A0.990
C3—C41.416 (4)C16—H16B0.990
C5—C61.347 (4)C17—C181.527 (6)
C7—C81.346 (4)C17—H17A0.990
C9—C101.526 (4)C17—H17B0.990
C9—H9A0.990C18—H18A0.980
C9—H9B0.990C18—H18B0.980
C10—C111.515 (4)C18—H18C0.980
C3—S1—C593.71 (13)C12—C11—H11A108.7
C4—S2—C593.67 (13)C10—C11—H11B108.7
C6—S3—C793.81 (13)C12—C11—H11B108.7
C6—S4—C893.95 (12)H11A—C11—H11B107.6
C7—S5—C999.46 (13)C13—C12—C11112.3 (3)
C8—S6—C14100.71 (14)C13—C12—H12A109.1
C1—N1—C2111.0 (2)C11—C12—H12A109.1
C1—N1—H1B124.5C13—C12—H12B109.1
C2—N1—H1B124.5C11—C12—H12B109.1
N1—C1—C3106.8 (3)H12A—C12—H12B107.9
N1—C1—H1A126.6C12—C13—H13A109.5
C3—C1—H1A126.6C12—C13—H13B109.5
N1—C2—C4106.6 (3)H13A—C13—H13B109.5
N1—C2—H2A126.7C12—C13—H13C109.5
C4—C2—H2A126.7H13A—C13—H13C109.5
C1—C3—C4107.7 (3)H13B—C13—H13C109.5
C1—C3—S1135.5 (2)C15—C14—S6114.4 (2)
C4—C3—S1116.70 (19)C15—C14—H14A108.7
C2—C4—C3107.8 (2)S6—C14—H14A108.7
C2—C4—S2134.9 (2)C15—C14—H14B108.7
C3—C4—S2117.3 (2)S6—C14—H14B108.7
C6—C5—S2121.49 (19)H14A—C14—H14B107.6
C6—C5—S1121.7 (2)C14—C15—C16115.5 (3)
S2—C5—S1116.81 (15)C14—C15—H15A108.4
C5—C6—S4123.0 (2)C16—C15—H15A108.4
C5—C6—S3124.36 (19)C14—C15—H15B108.4
S4—C6—S3112.63 (14)C16—C15—H15B108.4
C8—C7—S5126.3 (2)H15A—C15—H15B107.5
C8—C7—S3116.7 (2)C17—C16—C15113.8 (3)
S5—C7—S3116.95 (15)C17—C16—H16A108.8
C7—C8—S6126.4 (2)C15—C16—H16A108.8
C7—C8—S4116.47 (19)C17—C16—H16B108.8
S6—C8—S4117.02 (16)C15—C16—H16B108.8
C10—C9—S5114.20 (19)H16A—C16—H16B107.7
C10—C9—H9A108.7C16—C17—C18113.4 (3)
S5—C9—H9A108.7C16—C17—H17A108.9
C10—C9—H9B108.7C18—C17—H17A108.9
S5—C9—H9B108.7C16—C17—H17B108.9
H9A—C9—H9B107.6C18—C17—H17B108.9
C11—C10—C9112.9 (2)H17A—C17—H17B107.7
C11—C10—H10A109.0C17—C18—H18A109.5
C9—C10—H10A109.0C17—C18—H18B109.5
C11—C10—H10B109.0H18A—C18—H18B109.5
C9—C10—H10B109.0C17—C18—H18C109.5
H10A—C10—H10B107.8H18A—C18—H18C109.5
C10—C11—C12114.4 (2)H18B—C18—H18C109.5
C10—C11—H11A108.7
C2—N1—C1—C30.8 (3)C8—S4—C6—S324.26 (16)
C1—N1—C2—C40.7 (3)C7—S3—C6—C5155.3 (2)
N1—C1—C3—C40.5 (3)C7—S3—C6—S424.44 (15)
N1—C1—C3—S1177.5 (2)C9—S5—C7—C8111.5 (2)
C5—S1—C3—C1174.7 (3)C9—S5—C7—S371.14 (17)
C5—S1—C3—C48.5 (2)C6—S3—C7—C815.2 (2)
N1—C2—C4—C30.4 (3)C6—S3—C7—S5167.21 (16)
N1—C2—C4—S2179.1 (2)S5—C7—C8—S61.7 (4)
C1—C3—C4—C20.1 (3)S3—C7—C8—S6175.67 (16)
S1—C3—C4—C2177.7 (2)S5—C7—C8—S4177.86 (16)
C1—C3—C4—S2178.89 (19)S3—C7—C8—S40.5 (3)
S1—C3—C4—S21.2 (3)C14—S6—C8—C7120.3 (2)
C5—S2—C4—C2174.6 (3)C14—S6—C8—S463.56 (19)
C5—S2—C4—C36.8 (2)C6—S4—C8—C714.5 (2)
C4—S2—C5—C6169.6 (2)C6—S4—C8—S6168.99 (16)
C4—S2—C5—S112.86 (17)C7—S5—C9—C10102.3 (2)
C3—S1—C5—C6169.1 (2)S5—C9—C10—C1170.0 (3)
C3—S1—C5—S213.40 (17)C9—C10—C11—C12170.6 (2)
S2—C5—C6—S41.8 (3)C10—C11—C12—C13178.4 (2)
S1—C5—C6—S4179.20 (15)C8—S6—C14—C1566.9 (2)
S2—C5—C6—S3178.55 (15)S6—C14—C15—C1666.6 (3)
S1—C5—C6—S31.1 (3)C14—C15—C16—C1766.7 (4)
C8—S4—C6—C5155.5 (2)C15—C16—C17—C18175.1 (3)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds