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The title compound, C6H12N2S2, possesses a centre of symmetry with one-half of the mol­ecule in the asymmetric unit. The crystal structure has inter­molecular N—H...N and C—H...S contacts and intra­molecular S...N inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000389/at6073sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000389/at6073Isup2.hkl
Contains datablock I

CCDC reference: 298362

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.091
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.14 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 27.45 From the CIF: _reflns_number_total 878 From the CIF: _diffrn_reflns_limit_ max hkl 10. 4. 12. From the CIF: _diffrn_reflns_limit_ min hkl -10. -6. -12. TEST1: Expected hkl limits for theta max Calculated maximum hkl 12. 6. 12. Calculated minimum hkl -12. -6. -12.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Professors Yliana Yliana L\'opez and M. Eugenia Ochoa are the ones in charge of the synthesis and characterization of the compound. Professors Rosa Santillan and Norberto Farf\'an are the ones in charge of the research project. Professors Itzia I. Padilla-Mart\'inez and Efr\'en V. Garc\'ia-B\'aez are the ones in charge of the analysis of the crystal.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97(Sheldrick 1990); program(s) used to refine structure: SHELXL97 (Sheldrick 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,2'-Bi-1,3-thiazolidine top
Crystal data top
C6H12N2S2F(000) = 188
Mr = 176.30Dx = 1.415 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 600 reflections
a = 9.4931 (6) Åθ = 20–25°
b = 5.0070 (4) ŵ = 0.57 mm1
c = 9.5942 (8) ÅT = 293 K
β = 114.844 (3)°Block, colorless
V = 413.83 (6) Å30.15 × 0.10 × 0.08 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer
785 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.5°, θmin = 4.7°
Detector resolution: 9 pixels mm-1h = 1010
φ and ω scansk = 64
1332 measured reflectionsl = 1212
878 independent reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0315P)2 + 0.2832P]
where P = (Fo2 + 2Fc2)/3
878 reflections(Δ/σ)max < 0.001
70 parametersΔρmax = 0.62 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S10.14926 (5)0.70330 (12)0.09502 (5)0.0396 (2)
N30.13613 (18)0.4867 (4)0.20915 (17)0.0341 (5)
C20.0254 (2)0.6007 (4)0.0652 (2)0.0321 (5)
C40.0551 (3)0.3845 (5)0.2986 (2)0.0393 (6)
C50.0647 (3)0.5918 (5)0.2931 (2)0.0416 (7)
H20.074 (3)0.767 (5)0.032 (3)0.040 (6)*
H30.200 (3)0.616 (6)0.263 (3)0.052 (7)*
H4A0.003 (3)0.219 (6)0.248 (3)0.052 (7)*
H4B0.127 (3)0.348 (5)0.399 (3)0.044 (7)*
H5A0.014 (4)0.748 (6)0.360 (4)0.063 (8)*
H5B0.143 (3)0.520 (6)0.319 (3)0.059 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0326 (3)0.0513 (4)0.0326 (3)0.0101 (2)0.0116 (2)0.0016 (2)
N30.0297 (8)0.0434 (10)0.0240 (8)0.0024 (7)0.0061 (6)0.0001 (7)
C20.0294 (9)0.0355 (10)0.0282 (9)0.0017 (8)0.0089 (7)0.0002 (8)
C40.0413 (11)0.0402 (12)0.0309 (10)0.0050 (9)0.0099 (8)0.0034 (9)
C50.0400 (11)0.0539 (14)0.0338 (10)0.0036 (10)0.0185 (8)0.0001 (9)
Geometric parameters (Å, º) top
S1—C21.869 (2)C4—C51.524 (4)
S1—C51.8127 (19)C2—H21.06 (3)
N3—C21.455 (2)C4—H4A0.98 (3)
N3—C41.465 (3)C4—H4B0.94 (3)
N3—H30.89 (3)C5—H5A1.00 (3)
C2—C2i1.519 (3)C5—H5B0.95 (3)
S1···C4ii3.677 (2)C4···H3vi2.95 (3)
S1···N3i3.1213 (17)C4···H2i2.98 (3)
S1···H4Aiii3.02 (3)H2···S1iv3.12 (3)
S1···H2iv3.12 (3)H2···C4i2.98 (3)
S1···H5Bv2.91 (3)H2···H4Ai2.47 (4)
S1···H3ii3.03 (3)H3···N3vii2.36 (3)
S1···H4Bii3.12 (3)H3···C4vii2.95 (3)
N3···N3vi3.183 (3)H3···S1viii3.03 (3)
N3···N3vii3.183 (3)H4A···S1ix3.02 (3)
N3···S1i3.1213 (17)H4A···C2i3.04 (3)
N3···H3vi2.36 (3)H4A···H2i2.47 (4)
C4···S1viii3.677 (2)H4B···S1viii3.12 (3)
C2···H4Ai3.04 (3)H5B···S1x2.91 (3)
C2—S1—C592.59 (11)C2i—C2—H2107.5 (14)
C2—N3—C4110.20 (17)N3—C4—H4A106.5 (17)
C4—N3—H3108.2 (18)N3—C4—H4B109.6 (19)
C2—N3—H3108.1 (18)C5—C4—H4A110.1 (18)
S1—C2—C2i108.27 (14)C5—C4—H4B112.3 (17)
S1—C2—N3107.22 (13)H4A—C4—H4B110 (2)
N3—C2—C2i111.96 (17)S1—C5—H5A108.3 (19)
N3—C4—C5108.04 (19)S1—C5—H5B109.9 (16)
S1—C5—C4103.97 (14)C4—C5—H5A111 (2)
S1—C2—H2110.8 (15)C4—C5—H5B112.9 (19)
N3—C2—H2111.1 (15)H5A—C5—H5B110 (3)
C5—S1—C2—N30.29 (16)S1—C2—C2i—S1i180.00 (9)
C5—S1—C2—C2i121.26 (14)S1—C2—C2i—N3i62.02 (18)
C2—S1—C5—C423.39 (18)N3—C2—C2i—S1i62.02 (18)
C4—N3—C2—S124.8 (2)N3—C2—C2i—N3i180.00 (16)
C4—N3—C2—C2i93.8 (2)N3—C4—C5—S141.9 (2)
C2—N3—C4—C544.4 (2)
Symmetry codes: (i) x, y+1, z; (ii) x1/2, y+3/2, z1/2; (iii) x, y+1, z; (iv) x, y+2, z; (v) x1/2, y+1/2, z+1/2; (vi) x+1/2, y1/2, z+1/2; (vii) x+1/2, y+1/2, z+1/2; (viii) x+1/2, y+3/2, z+1/2; (ix) x, y1, z; (x) x1/2, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N3vii0.89 (3)2.36 (3)3.183 (3)153 (2)
C5—H5B···Sv0.95 (3)2.91 (3)3.842 (3)160.8 (6)
Symmetry codes: (v) x1/2, y+1/2, z+1/2; (vii) x+1/2, y+1/2, z+1/2.
 

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